Custom Monosaccharide Synthesis Service

As a leading provider for carbohydrate synthesis, Creative Biolabs provides high-quality custom synthesis of monosaccharide and its derivatives, with the most advanced chemical and enzymatic methods. From a few milligrams to multi-kilogram scale, our scientists are happy to share our cutting-edge technology and extensive expertise in custom synthesis.

Background of Monosaccharides

Fig.1 The structure of calcium-activated potassium channels. Distributed under Open Access license CC BY 3.0, from Wiki, without modification.

Monosaccharides are the simplest carbohydrates since they cannot be hydrolyzed into smaller carbohydrates. Chemically they are aldehydes or ketones possessing two or more hydroxyl groups, and are important as building blocks (such as D-ribose and 2-deoxy-D-ribose) for the synthesis of nucleic acids, as well as fuel molecules in glycolysis. The most common naturally occurring monosaccharides are D-glucose, D-fructose, D-mannose, and D-galactose among the hexoses and D-xylose and L-arabinose among the pentoses. Monosaccharides are classified according to three different characteristics: the location of their carbonyl group, the number of carbon atoms they contain, and their chiral property. If the carbonyl group is an aldehyde, the monosaccharide is an aldose. If the carbonyl group is a ketone, the monosaccharide is a ketose. Monosaccharides with three carbon atoms are called trioses and are the smallest monosaccharides, and four carbon atoms for tetroses, five carbons for pentoses, six carbons for hexoses, and so on.

Several derivatives of monosaccharides are important. Ascorbic acid is derived from glucose. Important sugar alcohols formed by the reduction of a monosaccharide, include sorbitol from glucose and mannitol from mannose. Glycosides derived from monosaccharides are widespread in nature, especially in plants. Amino sugars occur as components of glycolipids and in the chitin of arthropods.

Carbohydrates have diverse physiological functions, ranging from energy storage and structural integrity to cell signaling and the regulation of intracellular processes. Although many biomass-derived carbohydrates, which serve as renewable chemical feedstocks and building blocks, can be extracted on large scales, there are hundreds of distinct monosaccharides that typically cannot be isolated from their natural sources and must be synthesized through multistep chemical or enzymatic syntheses.

Synthesis of Natural, Non-natural Monosaccharides and Their Derivatives at Creative Biolabs

There are hundreds of monosaccharides that typically cannot be isolated from their natural sources and must instead be prepared through synthesis. As a long-term expert in glycan synthesis, Creative Biolabs owned lots of scientists who are proficient in custom synthesis of monosaccharide and its derivatives through multi-step chemical or enzymatic synthesis. Bioactive monosaccharide and its derivatives, such as site-specifically hydroxyl group modified monosaccharide, stereoisomer and regioisomer, can be synthesized and used as pharmaceuticals, including antiviral, antibacterial, anticancer and cardiac drugs. Our synthetic strategy provides concise and potentially extensive access to this valuable class of compounds.

• Monosaccharides with chemical modification

Synthesis of monosaccharide with chemical modifications, such as reducing terminal or individual functional group in monosaccharide by acylation, various fluorescence-labeling, PEGylations and biotinylation, etc.

• Labeled monosaccharide

Synthesis of stable isotope-labeled carbohydrates containing ¹³C, ²H, ¹⁵N, or ¹⁸O.

• General list of monosaccharides and their derivatives

Highlights

• Multi-step chemical or enzymatic synthesis
• Synthesis of monosaccharide and its derivatives with bioactivity, such as antiviral, antibacterial, anticancer, etc.
• cGMP manufacture
• Full analytical capability

Enriched with experience and state-of-the-art facilities, Creative Biolabs provides top-quality custom synthesis of monosaccharide and its derivatives. We offer turn-key or ala carte services customized to our client’s needs. Please contact us for more information and a detailed quote.

Published data

Sugar esters have a variety of biological activities, such as antifungal, antibacterial, and antitumor properties, which are expected to become potential antifungal and antibacterial agents for pharmaceutical and cosmetic applications. It has been pointed out in the literature that menthol and 3-(2-furyl)acrylic acid esters derivatives can be used as antibacterial agents, but their poor water solubility and low biological activity limit their application scope. While most monosaccharides are easily soluble in water and can be quickly transferred and utilized in the body. In this study, the author used menthol and 3-(2-furyl)acrylic acid as research objects, and under mild reaction conditions, designed and synthesized a series of water-soluble monosaccharide esters, including menthyloxycarbonyl monosaccharide esters II a–f and 3-(2-furyl)acrylate monosaccharide esters I a–f, and the structure of various synthesized monosaccharide esters were characterized by mass spectrometry, nuclear magnetic resonance, and infrared spectroscopy. In addition, the authors also evaluated the antibacterial and antifungal activities of these monosaccharide esters against five strains in vitro, and the results showed that compounds I f and II f exhibited significant antifungal effects against all tested strains.

Fig.1 Synthesis steps of target monosaccharide esters I a-f and II a-f.¹

FAQs

Q1: How do you ensure high yield and purity of monosaccharide synthesis?

A1: At Creative Biolabs, we utilize advanced chemical and enzymatic methods to maximize yield and purity. Our multi-step synthesis processes are carefully designed and optimized for each specific project. We employ state-of-the-art analytical techniques such as HPLC, NMR, and mass spectrometry to monitor the synthesis process and verify the purity and structure of the final product. Our stringent quality control ensures that each batch meets the high standards required for research and industrial applications.

Q2: What specific chemical modifications can you perform on monosaccharides?

A2: We provide a variety of chemical modification services, including but not limited to functional group modifications such as sulfation, phosphorylation, acylation, fluorescent labeling, and biotinylation. These modifications are used to enhance the biological activity and solubility of monosaccharides, making them widely applied in fields such as drug development and biochemical research.

Q3: How do you ensure the stereochemistry of synthesized monosaccharides?

A3: Stereochemistry is critical to the biological activity of monosaccharides. We achieve precise stereocontrol in our synthesis by using stereospecific reagents, catalysts, and enzymatic methods that favor the formation of the desired stereoisomer. Each step of the synthetic process is carefully monitored and verified using chiral analytical techniques to ensure that the correct stereochemistry is obtained.

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Reference

1. Shen, Yi, et al. "Synthesis, characterization, antibacterial and antifungal evaluation of novel monosaccharide esters." Molecules 17.7 (2012): 8661-8673. Distributed under Open Access license CC BY 3.0, without modification.

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