Fact-checked by Grok 2 weeks ago

Hexose

A hexose is a monosaccharide, or simple sugar, consisting of six carbon atoms and having the molecular formula C₆H₁₂O₆.^[1] With a molecular weight of 180.16 g/mol, hexoses typically exist in cyclic forms such as pyranose or furanose rings in biological systems, and they serve as fundamental units in carbohydrate metabolism and energy production across living organisms.^[1] Hexoses are classified into aldohexoses, which feature an aldehyde group at carbon 1, and ketohexoses, which have a ketone group at carbon 2.^[2] Aldohexoses possess 16 possible stereoisomers due to four chiral centers, while ketohexoses have 8, with the D-enantiomers being predominant in nature.^[2] These stereoisomers differ in their configuration at the chiral carbons, influencing their biological functions and interactions. Among the most abundant and biologically significant hexoses are D-glucose, D-galactose, and D-fructose, all sharing the formula C₆H₁₂O₆ but varying in structure and sweetness.^[3] D-glucose, an aldohexose also known as blood sugar or dextrose, is the primary energy source for cells, derived from dietary carbohydrates and photosynthesis, and maintained in human blood plasma at 70–99 mg/dL (fasting).^[3]^[4] D-galactose, another aldohexose, is obtained from the breakdown of lactose in milk and plays a key role in the synthesis of glycolipids, particularly in the myelin sheath of brain and nerve cells, earning it the nickname "brain sugar."^[3] D-fructose, a ketohexose found in high concentrations in fruits (up to 40% in honey) and known as levulose due to its levorotatory optical rotation of -92.4°, is the sweetest natural sugar, approximately 1.7 times sweeter than sucrose, and serves as an alternative energy source in metabolism.^[3] In biochemistry, hexoses are central to processes like glycolysis, the pentose phosphate pathway, and glycoconjugate formation, where glucose is stored as glycogen in animals or starch in plants for energy reserves.^[2] Their transport and metabolism are tightly regulated, as seen in microbial systems like Escherichia coli, where β-D-glucose acts as a key metabolite.^[1] Disruptions in hexose processing, such as in galactosemia, highlight their critical role in human health.^[5]

Definition and Nomenclature

Definition

Hexoses are a class of monosaccharides consisting of six carbon atoms and having the molecular formula C6H12O6; they can exist in either open-chain or cyclic configurations.^[6] These simple sugars are distinguished from other monosaccharides by the number of carbon atoms in their backbone, such as pentoses with five carbons or heptoses with seven, and hexoses represent the most abundant form encountered in nature.^[7]^[8] In biological systems, hexoses function primarily as energy sources, readily metabolized to provide fuel for cellular processes, and as fundamental building blocks for synthesizing polysaccharides and other complex carbohydrates.^[9] They occur as structural isomers including aldoses, which possess an aldehyde group, and ketoses, which contain a ketone group.^[10] The term "hexose" emerged in the late 19th century amid the pioneering work of Emil Fischer, who systematically classified carbohydrates based on chain length and functional groups during his studies of sugar stereochemistry.^[11]

Nomenclature

Hexoses, as six-carbon monosaccharides, are systematically named using the stem "hexose" derived from the corresponding alkane "hexane" by replacing the final "-ane" with "-ose".^[12] Aldohexoses, which possess an aldehyde group, are identified by the prefix "aldo-" attached to the stem name, with the carbonyl positioned at carbon 1 by convention; for instance, aldohexose denotes a hexose with the aldehyde at C-1.^[13] Ketohexoses, featuring a ketone group, use the prefix "keto-" followed by the position of the carbonyl, commonly at C-2, as in 2-ketohexose.^[13] The absolute configuration of hexoses is designated as D- or L- based on the Fischer projection convention, where the series is determined by the orientation of the hydroxyl group at the highest-numbered asymmetric carbon (the penultimate carbon) relative to D- or L-glyceraldehyde; in the D-series, this hydroxyl is on the right, and in the L-series, on the left.^[14] In the open-chain form, carbon atoms are numbered starting from the carbonyl carbon as C-1 and proceeding to the terminal CH₂OH group as C-6 for hexoses, ensuring consistent structural reference across representations.^[14] According to IUPAC recommendations, the full systematic name for the open-chain form of an aldohexose incorporates the R/S descriptors for each chiral center along with the functional group nomenclature; for example, D-glucose is named (2R,3S,4R,5R)-2,3,4,5,6-pentahydroxyhexanal.^[13]^[15] This approach prioritizes the aldehydic function as the parent chain, with hydroxy substituents at the specified positions.^[13]

Structural Features

Open-Chain Form

The open-chain form of a hexose represents its linear, acyclic structure, typically depicted using the Fischer projection convention, which arranges the carbon chain vertically with the most oxidized carbon (carbonyl group) at the top and the hydroxyl groups attached to chiral carbons shown as horizontal lines.^[16] In this projection, the vertical bonds extend away from the viewer, while horizontal bonds project toward the viewer, providing a standardized 2D representation of the 3D configuration.^[17] For aldohexoses, the open-chain structure features an aldehyde group at carbon 1 (C1), hydroxyl groups on carbons 2 through 5 (C2–C5), and a hydroxymethyl group (CH₂OH) at carbon 6 (C6), resulting in the general formula:

\begin{align*} &\ce{H-C=O}\\ &|\quad\quad\\ &(\ce{CHOH})_4\\ &|\quad\quad\\ &\ce{CH2OH} \end{align*}

^[18] This configuration yields four chiral centers at C2–C5, allowing for $2^4 = 16 possible stereoisomers.^[19] In contrast, ketohexoses possess a ketone group typically at C2, flanked by hydroxymethyl groups at both C1 and C6, with hydroxyl groups on C3–C5, creating three chiral centers at C3–C5 and thus $2^3 = 8 stereoisomers.^[19] In aqueous solution, cyclic structures predominate and equilibrate with the open-chain form.^[17]

Cyclic Forms

In aqueous solution, hexoses predominantly exist in cyclic forms resulting from intramolecular nucleophilic addition reactions that form hemiacetals or hemiketals.^[20] For aldohexoses, the aldehyde carbonyl at C1 reacts with the hydroxyl group at C5 to generate a six-membered pyranose ring, while for ketohexoses, the ketone carbonyl at C2 reacts with the hydroxyl at C5 (yielding a five-membered furanose ring) or at C6 (yielding a six-membered pyranose ring).^[10] These cyclizations create a new stereogenic center at the anomeric carbon—C1 in aldoses and C2 in ketoses—producing two diastereomers known as anomers.^[20] In Haworth projections, which depict the cyclic forms as planar rings, the α-anomer has the anomeric hydroxyl group oriented below the ring plane, whereas the β-anomer has it above the plane.^[10] Pyranose rings adopt a chair conformation in three dimensions, which is more stable than the boat form due to minimized steric interactions and angle strain. Stability is further enhanced when bulky substituents, such as hydroxyl groups, occupy equatorial positions rather than axial ones, as seen in the all-equatorial β-D-glucopyranose chair form.^[10] The α- and β-anomers, along with the open-chain form as a minor equilibrium component, interconvert through ring opening and reclosure in a process termed mutarotation, which is observable as a change in optical rotation.^[20] For example, freshly dissolved α-D-glucopyranose exhibits a specific rotation of +112°, which decreases to an equilibrium value of +52.7° as the mixture of forms establishes. Furanose forms are less prevalent in free hexoses compared to pyranose but appear in certain derivatives, such as the fructose moiety in sucrose.^[10]

Classification

Aldohexoses

Aldohexoses are a subclass of hexoses characterized by an aldehyde group at carbon 1 and four chiral centers at carbons 2 through 5, resulting in 2^4 = 16 possible stereoisomers: 8 in the D-series and 8 in the L-series.^[21]^[22] The D- and L-designations refer to the absolute configuration at the penultimate carbon (C5 in aldohexoses), determined using Cahn-Ingold-Prelog (CIP) priority rules, where the D-series corresponds to the (R) configuration at C5, analogous to D-glyceraldehyde.^[23] D-Glucose serves as the reference aldohexose, predominant in nature, and exists primarily in cyclic forms; in its β-D-glucopyranose conformation, all hydroxyl substituents are equatorial, conferring exceptional stability due to minimized steric interactions.^[24] Other common D-aldohexoses include D-mannose, an epimer of D-glucose differing in configuration at C2, and D-galactose, an epimer at C4; less abundant examples are D-allose (differing from glucose at C3), D-altrose, D-gulose, D-idose, and D-talose.^[21] Epimers such as these arise from inversion at a single chiral center, altering their physical and biochemical properties while maintaining the aldohexose framework. Aldohexoses are synthesized via the Kiliani-Fischer synthesis, which extends aldopentoses by adding a carbon atom to the aldehyde group through cyanohydrin formation followed by hydrolysis, yielding two epimeric aldohexoses that differ at the new C2 chiral center.^[25] Optical activity distinguishes aldohexoses, with specific rotations measured in aqueous equilibrium mixtures accounting for mutarotation between α- and β-anomers. For instance, D-glucose exhibits an equilibrium specific rotation of +52.7°, D-mannose +14.2°, and D-galactose +80.2°, reflecting their distinct stereochemical configurations and anomeric equilibria.^[26]^[27]

Ketohexoses

Ketohexoses are hexoses featuring a ketone group at the C2 position, distinguishing them from aldohexoses by the absence of an aldehyde at C1 and the presence of three chiral centers at C3, C4, and C5.^[28] This configuration yields four stereoisomers in the D-series and four in the L-series, for a total of eight possible ketohexoses.^[28] Unlike aldohexoses, which predominantly adopt six-membered pyranose rings, ketohexoses like fructose show a notable tendency toward five-membered furanose rings due to the enhanced stability of these structures in ketose configurations.^[29] The most prominent example is D-fructose, commonly occurring in its β-D-fructofuranose form, where the furanose ring forms between C2 and C5, with hydroxymethyl groups (-CH₂OH from C1 at C2 and from C6 at C5).^[30] Other key D-ketohexoses include D-psicose (the C3-epimer of D-fructose), D-sorbose (the C5-epimer), and D-tagatose (the C4-epimer), each exhibiting distinct configurations at the chiral centers that influence their biological roles and reactivity.^[28] D-fructose stands out for its sensory properties, possessing a relative sweetness 1.2 to 1.8 times that of sucrose on a molar basis, attributed to its interaction with sweet taste receptors, and it is levorotatory, with an equilibrium specific rotation of approximately -92° in aqueous solution.^[31]^[32] Ketohexoses are typically synthesized through the Lobry de Bruyn–van Ekenstein transformation, an base-catalyzed isomerization that proceeds via a common enediol intermediate, enabling interconversion between aldoses like D-glucose and D-mannose and the ketohexose D-fructose under mild alkaline conditions.^[33] This reversible reaction, first described in the late 19th century, is widely used in industrial processes to produce fructose from glucose and highlights the dynamic equilibrium among these monosaccharides in solution.^[33]

Modified Hexoses

Keto Variants

Keto variants of hexoses encompass those with the carbonyl group positioned at carbons other than the conventional C2, rendering them rare and typically transient due to heightened reactivity. Among these, 3-ketohexoses, bearing the ketone at C3, exhibit reduced stability compared to 2-ketohexoses, primarily owing to their propensity for enolization at the adjacent C2-C3 bond, which facilitates reversion to more stable 2-keto or aldose forms via common enediol intermediates. This tautomerism is exacerbated in aqueous environments, where 3-keto-D-glucose, for instance, equilibrates among multiple isomeric forms, including enols, limiting its persistence.^[34] Representative examples of 3-ketohexoses include synthetic 3-keto-D-glucose and its mannose epimer, prepared through selective oxidation, as well as 3-keto-levoglucosan, a cyclic derivative generated enzymatically from levoglucosan. In bacterial metabolism, 3-keto-levoglucosan functions as a key intermediate in the catabolism of levoglucosan—a pyrolysis product of cellulose—catalyzed by levoglucosan dehydrogenase, which oxidizes the substrate at C3 before subsequent hydration and reduction steps yield glucose.^[34] Such intermediates underscore the role of 3-ketohexoses in microbial adaptation to environmental carbohydrates, though their isolation remains challenging due to instability. Synthesis of 3-ketohexoses poses significant hurdles, often relying on enzymatic oxidation of the C3 hydroxyl group using oxidases like pyranose oxidase, which achieves high yields (up to 80%) under controlled conditions such as low temperature and neutral pH.^[34] Chemical methods, involving protection of other hydroxyls followed by selective oxidation, are similarly employed but complicated by the compounds' lability; for example, 3-keto-levoglucosan decomposes via β-elimination at the C1-C5 positions, with a half-life of approximately 16 hours at pH 7 and 30°C, though it remains stable in acidic media.^[34] Ketohexoses with the carbonyl at other positions, such as C4 or C5, are exceedingly rare in free form owing to even greater instability and are predominantly encountered as enzyme-bound biosynthetic intermediates. For instance, 4-ketohexoses like UDP-4-keto-glucose arise transiently during the conversion of UDP-glucose to UDP-galactose by UDP-glucose 4-epimerase, involving NAD+-dependent oxidation at C4 followed by reduction.^[35] Unlike standard ketohexoses like fructose, these variants rarely accumulate, emphasizing their ephemeral nature in biological contexts.

Deoxyhexoses

Deoxyhexoses constitute a subclass of hexoses characterized by the replacement of one or more hydroxyl groups with hydrogen atoms, yielding a typical molecular formula of C₆H₁₂O₅ for monodeoxy variants and altering their chemical properties compared to standard hexoses.^[36] These modifications most commonly occur at the C-6 position in natural deoxyhexoses, converting the primary alcohol to a methyl group, though deoxygenations at C-2, C-3, or C-4 are documented in specialized compounds.^[36] The stereochemistry at unmodified chiral centers is preserved from the parent hexose, maintaining configurational similarity to aldohexoses like galactose or mannose.^[37] Prominent natural examples include L-fucose, known chemically as 6-deoxy-L-galactose, which serves as a terminal sugar in N- and O-linked glycans on mammalian cell surfaces and in plant glycoproteins.^[38] Another widespread deoxyhexose is L-rhamnose, or 6-deoxy-L-mannose, integral to plant cell wall pectins such as rhamnogalacturonan I and II, where it links galacturonic acid residues and influences wall rigidity. In microbial contexts, daunosamine—a 3-amino-3,6-dideoxy-D-mannose—occurs as a glycosyl component in anthracycline antibiotics like daunorubicin, produced by Streptomyces peucetius.^[39] Synthetic analogs, such as 2-deoxy-D-glucose, mimic D-glucose but lack the 2-hydroxyl, enabling targeted biochemical studies. Biosynthesis of deoxyhexoses generally proceeds through nucleotide diphosphate (NDP)-sugar pathways, starting from common hexose precursors like glucose or mannose. For L-fucose, the pathway begins with GDP-D-mannose, which undergoes 4,6-dehydration by GDP-mannose 4,6-dehydratase to form GDP-4-keto-6-deoxy-D-mannose, followed by epimerization and reduction via GDP-fucose synthase to yield GDP-L-fucose.^[40] L-rhamnose synthesis mirrors this, involving GDP-4,6-dehydratase-mediated dehydration of GDP-D-mannose to GDP-4-keto-6-deoxy-D-mannose, then NADPH-dependent reduction by a 4-keto reductase to GDP-L-rhamnose.^[41] In bacteria, daunosamine is assembled from dTDP-D-glucose through sequential deoxygenation at C-3 and C-6, amination at C-3 by a transaminase, and methyltransferase activity, culminating in dTDP-L-daunosamine.^[39] These sugars find applications in therapeutics and research due to their modified reactivity. 2-Deoxy-D-glucose functions as a glycolysis inhibitor by competitively binding hexokinase, forming 2-deoxy-D-glucose-6-phosphate that accumulates and blocks phosphoglucose isomerase, thereby depleting cellular ATP in glucose-dependent cells like tumors.^[42] Daunosamine, when glycosidically linked to the aglycone in daunorubicin, enhances the drug's intercalation into DNA and improves its membrane permeability, underpinning its efficacy as an anticancer agent.^[43]

Chemical Properties

Reactivity

Hexoses, as monosaccharides containing six carbon atoms, exhibit reactivity primarily driven by their carbonyl (aldehyde or ketone) and multiple hydroxyl functional groups. In aldohexoses, the aldehyde group at C1 undergoes nucleophilic addition reactions more readily than the ketone group at C2 in ketohexoses, owing to greater electrophilicity and reduced steric hindrance around the carbonyl carbon.^[44] These carbonyls are also susceptible to oxidation; for instance, aldohexoses like glucose are oxidized to aldonic acids such as gluconic acid using Tollens' reagent, which selectively targets the aldehyde in the open-chain form present in equilibrium with the cyclic structure./22%3A_The_Organic_Chemistry_of_Carbohydrates/22.06%3A_The_Oxidation-Reduction_Reactions_of_Monosaccharides) Ketohexoses, while less reactive to mild oxidants, can isomerize under basic conditions to aldoses, enabling similar oxidation./22%3A_The_Organic_Chemistry_of_Carbohydrates/22.06%3A_The_Oxidation-Reduction_Reactions_of_Monosaccharides) The hydroxyl groups in hexoses confer weak acidity, with pKa values typically ranging from 12 to 14, reflecting their alcoholic nature and enabling reactions such as esterification with carboxylic acids or ether formation under appropriate conditions.^[45] The anomeric hydroxyl at C1 in cyclic forms shows slightly higher acidity (pKa around 12.3 for glucose) due to its position adjacent to the ring oxygen, influencing reactivity at this site.^[46] This acidity allows deprotonation in strongly basic media, facilitating further transformations. At the anomeric carbon, reactivity is pronounced, particularly in the open-chain form where the carbonyl is free, but persists in cyclic hemiacetals through equilibrium, leading to glycoside formation via nucleophilic attack by alcohols on the protonated anomeric carbon.^[47] The cyclic vs. open-chain equilibrium modulates overall reactivity, with the small proportion of open-chain species (less than 1% for glucose) sufficient to drive many responses.^[48] Hexoses are sensitive to heat and acid; upon heating above 150°C, they undergo caramelization, a non-enzymatic browning involving dehydration, fragmentation, and polymerization to form colored, flavorful compounds like hydroxymethylfurfural from glucose.^[49] In acidic conditions, the cyclic rings hydrolyze to the open-chain form, increasing carbonyl availability and reactivity.^[50] All hexoses act as reducing sugars because the equilibrium with their open-chain tautomers provides a free carbonyl group capable of reducing Cu²⁺ in Fehling's or Benedict's solutions to Cu₂O, producing a red precipitate./09%3A_Lab_9-_Tests_for_Carbohydrates) This property holds for both aldo- and ketohexoses, as ketohexoses isomerize to aldoses under the test's alkaline conditions.^[51]

Common Reactions

Hexoses undergo glycosylation reactions, where the anomeric carbon of one hexose molecule forms a glycosidic bond with a hydroxyl group of another molecule or aglycone, leading to disaccharides or more complex carbohydrates. For instance, two glucose molecules can condense to form maltose through an α-1,4-glycosidic linkage, eliminating water in a dehydration process.^[52] Oxidation of hexoses can be complete or selective, depending on the reagents used. Complete oxidation with concentrated nitric acid oxidizes both the aldehyde group (in aldoses) and the primary alcohol at C6 to carboxylic acids, yielding saccharic acids such as glucaric acid from glucose. The reaction proceeds as follows:

\ce{C6H12O6 (glucose) + 3 HNO3 -> HOOC-(CHOH)4-COOH (glucaric acid) + 3 NO2 + 3 H2O}

^[53] Selective oxidation targets only the aldehyde group to form aldonic acids or the C6 hydroxyl to produce uronic acids, such as glucuronic acid from glucose, often using milder agents like bromine water for the former or enzymatic/templated methods for the latter.^[54] Reduction of hexoses involves the carbonyl group being converted to a hydroxyl, producing alditols. For example, glucose is reduced to sorbitol using sodium borohydride (NaBH₄) as a mild reducing agent, which donates hydride to the carbonyl carbon.^[55] The Kiliani-Fischer synthesis lengthens the carbon chain of an aldose by one unit, converting an aldopentose to two epimeric aldohexoses. This involves addition of hydrogen cyanide (HCN) to the aldehyde group, forming cyanohydrins, followed by hydrolysis to aldonic acids and reduction to the aldoses.^[56] In contrast, the Ruff degradation shortens the chain of an aldose by one carbon. The process oxidizes the aldose to an aldonic acid with bromine water, forms the calcium salt, and then oxidizes with hydrogen peroxide and ferric acetate to decarboxylate, yielding the lower aldose.^[57]

Biological Significance

Natural Occurrence

Hexoses are ubiquitous in nature, serving as fundamental building blocks of life across diverse organisms. They constitute a significant portion of Earth's biomass, primarily in polymerized forms such as starch, cellulose, and glycogen, with plant-derived carbohydrates forming the majority of global biomass (plants account for ≈82% of total biomass, largely as hexose polymers).^[58] Glucose, the most abundant hexose, is the primary product of photosynthesis via the Calvin-Benson cycle, where carbon dioxide is fixed into glyceraldehyde-3-phosphate and subsequently converted into glucose as the key carbohydrate output in plants.^[59] In animals, glucose circulates as the principal blood sugar, maintaining energy homeostasis, and forms the monomeric unit of storage polysaccharides like glycogen in liver and muscle tissues.^[60] Additionally, glucose polymers starch and cellulose provide energy reserves in plants and structural support in plant cell walls, respectively, underscoring its role in terrestrial ecosystems.^[61] Fructose, a ketohexose, is prevalent in plant-derived sources, particularly fruits and floral nectars, where it contributes to sweetness and energy storage. In honey, fructose comprises up to 50% of the total sugar content, often exceeding glucose in concentration and aiding in the preservation of this natural product through its hygroscopic properties.^[62] Fructose also combines with glucose to form sucrose, the predominant disaccharide in many plants, facilitating efficient transport and storage of carbohydrates in sources like sugarcane and beets.^[63] Galactose, an aldohexose, is notably found in lactose, the primary carbohydrate in mammalian milk, where it pairs with glucose to provide essential energy for neonatal development. In plants, galactose integrates into galactolipids, which form the majority of membrane lipids in chloroplasts and thylakoids, supporting photosynthetic processes and cellular integrity.^[64] Other hexoses, such as mannose, occur in specialized natural matrices; mannose is a key component of plant gums like guar and locust bean gum, where it contributes to viscous exudates for protection against environmental stress. It also features prominently in bacterial polysaccharides, such as those in biofilms and cell walls, enhancing microbial adhesion and structural diversity in ecosystems.^[65] From an evolutionary perspective, hexoses have been central to life since its origins, with prebiotic synthesis pathways like the formose reaction enabling the abiotic formation of sugars from formaldehyde under early Earth conditions, potentially seeding the carbohydrate pool for primordial metabolic networks.^[66]

Metabolism and Biosynthesis

In plants, glucose, a primary aldohexose, is biosynthesized from carbon dioxide and water through photosynthesis, a light-driven process that captures solar energy to fix CO₂ into organic compounds via the Calvin-Benson cycle, ultimately yielding glucose as a key product.^[67] In animals, glucose synthesis occurs via gluconeogenesis, a pathway that generates glucose from non-carbohydrate precursors such as lactate, glycerol, and glucogenic amino acids like alanine, primarily in the liver and kidneys to maintain blood glucose levels during fasting.^[68] This process reverses key steps of glycolysis but employs distinct enzymes to bypass irreversible reactions, ensuring efficient net production of glucose.^[69] Hexoses like glucose are catabolized primarily through glycolysis, a cytosolic pathway that begins with the phosphorylation of glucose to glucose-6-phosphate (G6P) by hexokinase, consuming one ATP molecule per glucose.^[70] Subsequent steps convert G6P to two molecules of pyruvate, generating four ATP and two NADH, resulting in a net yield of two ATP per glucose molecule under anaerobic conditions.^[71] Fructose, a ketohexose, follows a distinct route in the liver, where fructokinase phosphorylates it to fructose-1-phosphate (F1P) using ATP, and aldolase B then cleaves F1P into dihydroxyacetone phosphate (DHAP) and glyceraldehyde, with DHAP directly entering glycolysis.^[72] An alternative metabolic route for hexoses is the pentose phosphate pathway, which branches from G6P and serves dual purposes: the oxidative phase generates NADPH for reductive biosynthesis and antioxidant defense by oxidizing G6P to ribulose-5-phosphate, producing two NADPH molecules per glucose equivalent.^[73] The non-oxidative phase interconverts sugars, enabling the production of ribose-5-phosphate for nucleotide synthesis from glucose-derived intermediates without net NADPH generation.^[74] Industrially, glucose syrup is produced by enzymatic hydrolysis of starch from sources like corn, involving liquefaction with alpha-amylase followed by saccharification with glucoamylase to yield high-glucose content syrups used in food processing.^[75] High-fructose corn syrup is derived similarly, with additional glucose isomerization to fructose using xylose isomerase, achieving up to 55% fructose for sweetened beverages.^[76] In medicine, 2-deoxyglucose, a glucose analog and deoxyhexose, acts as an adjunct in cancer therapy by inhibiting glycolysis in tumor cells, enhancing the efficacy of radiotherapy and chemotherapy through glycolytic blockade and oxidative stress induction.^[42] Biosynthesis of deoxyhexoses, such as L-fucose, proceeds from GDP-mannose in a de novo pathway: GDP-mannose is first converted to GDP-4-keto-6-deoxy-D-mannose by GDP-mannose 4,6-dehydratase, followed by action of a bifunctional GDP-4-keto-6-deoxy-D-mannose epimerase/reductase, which epimerizes at C5 and reduces the keto group using NADPH to yield GDP-L-fucose for glycoprotein and glycolipid assembly.^[77] This pathway is conserved across eukaryotes and essential for fucosylation in cellular recognition processes.^[78]

References

[1]
Hexose | C6H12O6 | CID 206 - PubChem - NIH
Hexopyranose is a hexose. ChEBI bD-Glucose is a metabolite found in or produced by Escherichia coli (strain K12, MG1655).Missing: biochemistry | Show results with:biochemistry
[2]
Hexose Definition and Examples - Biology Online Dictionary
### Summary of Hexose from Biology Online Dictionary
[3]
7.2: Important Pentoses and Hexoses
### Summary of Hexoses
[4]
Classical Hereditary galactosemia: findings in patients and animal ...
Sep 13, 2023 · This review aims to report a comprehensive analysis of past studies and state of art research on galactosemia screening, its clinical and ...<|separator|>
[5]
CPC Definition - C13B PRODUCTION OF SUCROSE - USPTO
Hexose. A hexose is a monosaccharide with six carbon atoms having the chemical formula C6H12O6. Ketose. A ketose is a sugar containing one ketone group per ...
[6]
Carbohydrates
They are also classified as a triose, tetrose, pentose, hexose, or heptose on the basis of whether they contain three, four, five, six, or seven carbon atoms.
[7]
7. ANALYSIS OF CARBOHYDRATES
Most natural monosachharides have either five (pentoses) or six (hexoses) carbon atoms. Commonly occurring hexoses in foods are glucose, fructose and galactose, ...
[8]
Oligosaccharides and Polysaccharides - Essentials of Glycobiology
Except in their roles as sources of energy for living organisms, sugars seldom occur in nature as monosaccharides. Instead, they serve as building blocks for ...
[9]
Carbohydrates - MSU chemistry
The most common carbohydrate is glucose (C6H12O6). Applying the terms defined above, glucose is a monosaccharide, an aldohexose (note that the function and ...
[10]
Historical Background and Overview - Essentials of Glycobiology
This chapter provides a historical background to the field of glycobiology and an overview of this book. General terms found in the volume are considered, ...
[11]
2-Carb-2
### Nomenclature Rules for Aldoses and Ketoses
[12]
NOMENCLATURE OF CARBOHYDRATES - iupac
The stem names for the aldoses with three to ten carbon atoms are triose, tetrose, pentose, hexose, heptose, octose, nonose, decose. The chain is numbered so ...
[13]
2-Carb-3 and 2-Carb-4
### Summary of Fischer Projections, D/L Series, and Carbon Numbering for Open-Chain Hexoses
[14]
https://iupac.qmul.ac.uk/2carb/03n04.html
[15]
https://pubchem.ncbi.nlm.nih.gov/compound/aldehydo-D-glucose
[16]
25.4: Configurations of Aldoses - Chemistry LibreTexts
Mar 17, 2024 · Aldohexoses have sixteen (24) possible stereoisomers. five pairs of D/L enantiomers called allose, altrose, glucose, mannose, gulose, idose, ...
[17]
25.4 Configurations of the Aldoses - Organic Chemistry | OpenStax
Sep 20, 2023 · Aldohexoses have four chirality centers and a total of 24 = 16 possible stereoisomers, or eight D,L pairs of enantiomers. The names of the ...
[18]
LON-CAPA CarbohydratesI
The letters R and S are the descriptors that the Cahn-Ingold-Prelog rules use to specify the disposition of substituents about a chiral center. In D ...
[19]
25.5 Cyclic Structures of Monosaccharides: Anomers - OpenStax
Sep 20, 2023 · Note that in β-D-glucopyranose, all the substituents on the ring are equatorial. Thus, β-D-glucopyranose is the least sterically crowded and ...
[20]
25.6: Reactions of Monosaccharides - Chemistry LibreTexts
Feb 24, 2025 · The Kiliani–Fischer synthesis lengthens the carbon chain of an aldose by one carbon atom. In doing this two new sugar epimers are created. The ...
[21]
Cyclic Structure of Glucose | CK-12 Foundation
Sep 30, 2025 · Specifically, pure α-glucose has a specific rotation of +112°, β-glucose +19°, and the equilibrium mixture in water settles at +52.7°. This ...
[22]
The specific rotation of α-D-galactose is 150.7 and that of β-D-g...
Jun 28, 2024 · The equation is: eq = ( x * α α) + ((1 - x ) * α β), where eq is the specific rotation at equilibrium, α is the specific rotation of α-d- ...
[23]
Ketohexose - an overview | ScienceDirect Topics
The chiral carbon atom at the hemiacetal center that forms in the cyclization reaction is called the anomeric carbon atom. Now let's consider the cyclic form of ...
[24]
Synthesis of Furandicarboxylic Acid Esters From Nonfood ... - NIH
The highest yields of HMF were achieved starting from d‐fructose, which has a higher preference for the furanose form (five‐membered ring) in aqueous solution ...<|control11|><|separator|>
[25]
beta-D-fructose | C6H12O6 | CID 439709 - PubChem - NIH
Beta-D-fructofuranose is a D-fructofuranose. It has a role as a mouse metabolite. It is an enantiomer of a beta-L-fructofuranose.
[26]
Relative sweetness of fructose compared with sucrose in healthy ...
Fructose is credited with some advantages over sucrose: it causes less of an increment in plasma glucose and insulin response, and the taste is sweeter.
[27]
D-Fructose | C6H12O6 | CID 2723872 - PubChem - NIH
D-Fructose | C6H12O6 | CID 2723872 - structure, chemical names, physical ... Specific optical rotation: -132 deg to -92 deg (c=2) @ 20 °C/D. Rapid and ...
[28]
Isomerization of 6-O-substituted glucose and fructose under neutral ...
Introduction. Aldose–ketose isomerization of reducing sugars, also known as the Lobry de Bruyn–van Ekenstein transformation, is a useful reaction to produce a ...
[29]
https://pmc.ncbi.nlm.nih.gov/articles/PMC5413837/
[30]
Deoxy Sugar - an overview | ScienceDirect Topics
Most naturally occurring deoxyhexoses are deoxygenated at the C6 position; however, further deoxygention at C2, C3 and C4 is also observed [3,6,59]. Although ...
[31]
Deoxy Sugar - an overview | ScienceDirect Topics
Deoxysugars are important structural components in numerous natural products, including glycoproteins, bacterial endotoxins, and secondary metabolites.
[32]
Biological functions of fucose in mammals - PMC - NIH
Fucose is a 6-deoxy hexose in the l-configuration found in a large variety of different organisms. In mammals, fucose is incorporated into N-glycans, O-glycans ...
[33]
In Vitro Reconstitution of the dTDP-l-Daunosamine Biosynthetic ...
Nov 9, 2021 · In an in vitro system, we have reconstituted the enzymes in the daunorubicin/doxorubicin pathway involved in the biosynthesis of dTDP-l-daunosamine.
[34]
Fucose: biosynthesis and biological function in mammals
L-fucose (6-deoxy-L-galactose) is a monosaccharide that is a common component of many N- and O-linked glycans and glycolipids produced by mammalian cells.Missing: occurrence | Show results with:occurrence
[35]
NDP-rhamnose biosynthesis and rhamnosyltransferases
Feb 18, 2021 · Rhamnose is an important 6-deoxy sugar present in many natural products, glycoproteins, and structural polysaccharides.
[36]
2-Deoxy-D-Glucose: A Novel Pharmacological Agent for Killing ...
The nonmetabolizable glucose analog 2-deoxy-D-glucose (2-DG) has shown promising pharmacological activities, including inhibition of cancerous cell growth ...
[37]
Daunosamine - an overview | ScienceDirect Topics
Daunosamine is defined as a sugar moiety that is linked to the planar anthraquinone chromophore in the anthracycline group of compounds, which are used in ...
[38]
[PDF] Carbohydrate analysis by high-performance anion-exchange ...
Glucose has a pKa of 12.28. When its anomeric hydroxyl is reduced to form sorbitol, its pKa increases to. 13.60, and when its anomeric hydroxyl is methylated to.
[39]
Determination of proton affinities and acidity constants of sugars
Jun 20, 2013 · Regarding the deprotonation processes (pKa), we found that the sugars' anomeric hydroxyls exhibit the highest acidity.
[40]
Glycosides - Chemistry Steps
The resulting carbocation is resonance stabilized and this explains why out of all the OH groups of the sugar, only the one on the anomeric carbon reacts.
[41]
Caramelization | American Society of Baking
Caramelization is a complex group of reactions that take place when sugars, either dry or in concentrated aqueous solutions, are subjected to high temperatures.
[42]
The Science of Caramelization - Food Chemistry Basics
Jun 18, 2021 · A more acidic or alkaline environment speeds up caramelization. It can also cause caramelization to start happening at a lower temperature ...
[43]
What Are Reducing Sugars? - Master Organic Chemistry
Sep 12, 2017 · A reducing sugar is a simple sugar containing a hemiacetal functional group. The ring-opened form reduces Cu2+ (Benedicts, Fehlings) and Ag+ ...
[44]
24.8: Disaccharides and Glycosidic Bonds - Chemistry LibreTexts
May 30, 2020 · This linkage is formed from the reaction of the anomeric carbon of one cyclic monosaccharide with the OH group of a second monosaccharide.Missing: reactivity | Show results with:reactivity
[45]
Sugar Oxidation, Saccharic and Oxalic Acids by the Nitric Acid ...
Aerobic oxidation of glucose to glucaric acid under alkaline-free conditions: Au-based bimetallic catalysts and the effect of residues in a hemicellulose ...
[46]
Uronic Acid - an overview | ScienceDirect Topics
Uronic acids are oxidized sugar acids with a carboxyl group, derived from the oxidation of the hydroxyl group on C6 of aldoses.
[47]
24.6: Reduction of Monosaccharides to Alditols - Chemistry LibreTexts
Jul 19, 2015 · Sodium borohydride reduction of an aldose makes the ends of the resulting alditol chain identical, HOCH2(CHOH)nCH2OH, thereby accomplishing the ...
[48]
22.8: Lengthening the Chain- The Kiliani-Fischer Synthesis
Jul 29, 2014 · The osazone reaction was developed and used by Emil Fischer to identify aldose sugars differing in configuration only at the alpha-carbon.
[49]
9.5 Degradation and Synthesis of Monosaccharides - KPU Pressbooks
Ruff degradation is the method to shorten the chain of monosaccharides by one carbon atom. It is a process that involves two steps, in which aldose is oxidized ...
[50]
The biomass distribution on Earth - PNAS
May 23, 2018 · We find that the biomass of plants dominates the biomass of the biosphere and is mostly located on land.Sign Up For Pnas Alerts · Results · Materials And Methods
[51]
Photosynthesis - PMC - PubMed Central - NIH
Oct 26, 2016 · The Calvin–Benson cycle uses ATP and NADPH to convert CO2 into carbohydrates (Figure 3), regenerating ADP and NADP+. The light and dark ...
[52]
Carbohydrate Metabolism - PMC - NIH
Animals lack enzymes that can break down the cellulose into smaller glucose molecules, but they can break down starch into smaller glucose molecules. Animals ...
[53]
Carbohydrates in Food-Producing Animal Nutrition
But glucose is an aldose (also called aldohexose) and fructose is a ketose, or a ketohexose. The three hexoses that are nutritionally and metabolically ...<|separator|>
[54]
Honey and Diabetes: The Importance of Natural Simple Sugars in ...
Feb 4, 2018 · Fructose content of honey varies from 21 to 43% and the fructose/glucose ratio from 0.4 to 1.6 or even higher [31–34]. Although fructose is the ...
[55]
Fructose | alimentarium
Fructose is a monosaccharide naturally present in fruit, vegetables and honey. When combined with glucose, it forms sucrose, commonly known as sugar.
[56]
Galactose in human metabolism, glycosylation and congenital ...
In milk, galactose is present in the form of lactose, a disaccharide formed ... plants and microbes, and (ii) glycosphingolipids, which instead contain ...<|separator|>
[57]
Mannose - an overview | ScienceDirect Topics
Mannose is an aldohexose in glycoproteins, obtained from plant polysaccharides. D-Mannose is a simple sugar that prevents bacterial adherence in the bladder.
[58]
Prebiotic Sugar Formation Under Nonaqueous Conditions and ... - NIH
Jun 20, 2019 · One of the plausible prebiotic synthesis routes is the formose network, which generates sugars from C1 and C2 carbon sources in basic aqueous ...
[59]
From the Photosynthesis to Hormone Biosynthesis in Plants - PMC
Apr 1, 2024 · Land plants produce glucose (C6H12O6) through photosynthesis by utilizing carbon dioxide (CO2), water (H2O), and light energy.
[60]
Gluconeogenesis - Chemistry LibreTexts
Jul 4, 2022 · Gluconeogenesis is the metabolic process by which organisms produce sugars (namely glucose) for catabolic reactions from non-carbohydrate precursors.
[61]
Tracking the carbons supplying gluconeogenesis - PMC - NIH
Gluconeogenic precursors come from noncarbohydrate sources, including lactate, glycerol, and amino acids. The two most relevant amino acids for gluconeogenesis ...
[62]
Glycolysis | Cellular respiration | Biology (article) - Khan Academy
Overall, glycolysis converts one six-carbon molecule of glucose into two three-carbon molecules of pyruvate. The net products of this process are two molecules ...
[63]
7.7: Glycolysis - Chemistry LibreTexts
May 12, 2024 · Glycolysis is a 10-step process converting glucose to pyruvate in the cytoplasm, with a preparatory phase requiring 2 ATP and a payoff phase ...
[64]
Fructose metabolism and metabolic disease - PMC - PubMed Central
F1P is metabolized to dihydroxyacetone phosphate (DHAP) and glyceraldehyde 3-phosphate (G3P), which enter the glycolytic/gluconeogenic metabolite pools (Figure ...
[65]
The pentose phosphate pathway in health and disease - PMC
The oxPPP converts glucose 6-phosphate into ribose 5-phosphate while making two molecules of NADPH. The non-oxidative branch (non-oxPPP) reversibly ...
[66]
13.4: Pentose Phosphate Pathway of Glucose Oxidation
Aug 23, 2025 · The non-oxidative branch of the pentose phosphate pathway (nonox-PPP) is responsible for forming simple sugars within the cell and maintaining ...
[67]
Industrial Glucose Syrup Production Process from Starch - Myande
Jul 23, 2025 · Glucose syrup is produced through a systematic, multi-step process that includes starch liquefaction, enzymatic saccharification, filtration, ...
[68]
Production Process - Sweeteners - Cargill
Glucose and glucose-fructose syrups are made by controlled hydrolysis of corn or wheat starch using acid and/or enzymes, similar to how the body digests ...
[69]
GDP-4-keto-6-deoxy-D-mannose epimerase/reductase ... - PubMed
The 'de novo' pathway of GDP-L-fucose biosynthesis from GDP-D-mannose involves a GDP-D-mannose 4,6 dehydratase (GMD) and a GDP-4-keto-6-deoxy-D-
[70]
GFUS - GDP-L-fucose synthase - Homo sapiens (Human) - UniProt
Catalyzes the two-step NADP-dependent conversion of GDP-4-dehydro-6-deoxy-D-mannose to GDP-fucose, involving an epimerase and a reductase reaction.