Monosaccharide Synthesis

Monosaccharides, indigestible sugar units, serve as metabolic energy hubs and building blocks for polysaccharides, nucleic acids, and glycoproteins. Their synthesis, modification, and analysis underpin advancements in pharmaceuticals, biotechnology, and food science. With years of deep research on carbohydrate chains in glycobiology and development of glycan analysis technologies, Creative Biolabs provides one-stop solutions from custom monosaccharide synthesis, modification to monosaccharide analysis, and we are willing to partner with you to facilitate your glycan-related research.

Enzymatic Synthesis of Monosaccharides

Enzymatic synthesis capitalizes on biological catalysts to achieve high selectivity under mild conditions.

• Glycosyltransferases transfer sugar moieties from activated donors (e.g., UDP-sugars) to acceptor molecules, enabling precise glycosidic bond formation critical for oligosaccharide and glycoconjugate assembly.
• Glycosidases, traditionally associated with hydrolysis, can reverse-engineer transglycosylation under optimized pH/solvent conditions, creating tailored glycosidic linkages.
• Epimerases facilitate chiral conversions (e.g., D-glucose to D-mannose), expanding precursor utility. This enzyme-driven flexibility reduces waste and avoids harsh chemical reagents.

Fig.1 Enzyme-based strategies for producing building blocks in glycan synthesis.^1,3

Chemical Synthesis of Monosaccharides

Chemical methods remain indispensable for complex sugar architectures:

• Kiliani–Fischer synthesis extends aldose chains via cyanohydrin intermediates, yielding epimer mixtures (e.g., D-glucose/D-mannose from D-arabinose). The three-step protocol—cyanohydrin formation, hydrolysis, and reduction—has been refined for scalability. The three-step process involves:
  • Cyanohydrin formation: An aldose reacts with hydrogen cyanide (HCN) to form a cyanohydrin.
  • Hydrolysis: The cyanohydrin undergoes hydrolysis to yield an aldonic acid.
  • Reduction: The aldonic acid is reduced to form a new aldose.
• Achmatowicz reaction converts furans to dihydropyrans, a versatile platform for natural product synthesis. Oxidation followed by rearrangement enables access to monosaccharides like ribose and derivatives for nucleoside drug development. The two general steps include:
  • Oxidation: A furan derivative is oxidized to form a dihydrofuran.
  • Rearrangement: The dihydrofuran rearranges into a dihydropyran structure.

Related Monosaccharides Synthesis Research

The Effect of Enhanced Growth Conditions on Monosaccharide Profiles in Algae

Research indicates that the monosaccharide composition of Ulva fenestrata changes when exposed to various abiotic factors including irradiance levels, temperature changes and different concentrations of nitrate and phosphate along with carbon dioxide partial pressure (pCO₂). Monosaccharide content rose when algae were cultivated in conditions with lowered nitrate levels and higher temperatures. The contents of iduronic acid and rhamnose rose by 70% and 26% respectively when conditions of higher irradiance and temperature were applied. The study demonstrates that by optimizing culture conditions we can control monosaccharide levels in algae to direct the production of algal polysaccharides with specific bioactivities.^2,3

Modifications for Monosaccharides

Creative Biolabs provides a complete range of glycan modification and labeling services which include phosphorylated, halogenated, and sialylated derivatives to support the development of antiviral drugs, cancer treatments, and cardiac medications.

Purification & Analysis of Monosaccharides

• Monosaccharides Purification: Normal-phase chromatography (polarity-based), affinity chromatography (lectin-based), and ion-exchange (charge-based) techniques isolate sugars with >95% purity.
• Monosaccharides Analysis: HPAEC-PAD quantifies sugars via pulsed amperometry (e.g., glucose/rhamnose detection in algae), while MS and CE resolve structural isomers. Recent work on Ulva. fenestrate employed a four-step eluent gradient to distinguish acidic sugars like iduronic acid.

Industrial Translation

• Pharmaceuticals: Glucose laurate (GLC12) and fructose laurate (FRU12) show antimicrobial activity (e.g., FRU12 inhibits S. aureus at 12.5%).
• Food: Sugar alcohols (sorbitol) replace sucrose in low-calorie products.
• Biotech: Fermentable monosaccharides from algae boost biofuel yields; chiral lactones derived from glucose enable biodegradable polymer synthesis.

Monosaccharides and Derivatives We Provide

With extensive experience in glycan synthesis, Creative Biolabs offers custom synthesis of monosaccharides and their derivatives through multi-step chemical or enzymatic processes. These bioactive monosaccharides, including site-specifically hydroxyl group-modified variants, stereoisomers, and regioisomers, are synthesized for pharmaceutical applications such as antiviral, antibacterial, anticancer, and cardiac therapies. Our strategic approach provides efficient and broad access to this valuable class of compounds. We are committed to provide various types of monosaccharides and their derivatives including:

Published Data

Researchers have studied the sugar composition of Ulva fenestrata, a type of green seaweed, by employing a two-step sulfuric acid hydrolysis technique. They utilized high-performance anion-exchange chromatography paired with pulsed amperometric detection (HPAEC-PAD) to quantify sugars like glucose, rhamnose, and iduronic acid. It is revealed that varying cultivation conditions led to significant differences in sugar content, especially in rhamnose and iduronic acid levels. The following graph outlines the eluent gradient program used in the HPAEC analysis, detailing the application of four different eluents and the post-column addition of a 300 mM NaOH solution.These insights highlight how external environmental factors can influence the sugar makeup of Ulva fenestrata. By adjusting these factors, it's possible to optimize the production of valuable sugars for various industrial uses.

Fig.2 Impact of environmental conditions on monosaccharide content in Ulva fenestrate.^2,3

FAQs

References

1. Dolan, Jonathan P., Sebastian C. Cosgrove, and Gavin J. Miller. "Biocatalytic approaches to building blocks for enzymatic and chemical glycan synthesis." JACS Au 3.1 (2022): 47-61. https://doi.org/10.1021/jacsau.2c00529
2. Olsson, Joakim, et al. "Cultivation conditions affect the monosaccharide composition in Ulva fenestrata." Journal of Applied Phycology 32.5 (2020): 3255-3263. https://doi.org/10.1007/s10811-020-02138-9
3. Distributed under Open Access license CC BY 4.0, without modification.

Related Services

Resources

• Monosaccharide Structure
• Monosaccharide Examples & Types
• Monosaccharide Properties
• Monosaccharide vs. Other Saccharides
• Monosaccharide Analysis
• Monosaccharide Function
• Monosaccharide & Blood Types
• Aldose & Ketose
• Pentose & Hexose
• Ribose & Deoxyribose

---