Custom Polysaccharide Synthesis Service

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The inherent structural and chemical variability of polysaccharides provide an enormous unexploited design space for the production of a range of new biobased materials. With world-leading technology platforms, plus years of experience in polysaccharide synthesis, Creative Biolabs is dedicated to helping our clients design and prepare high-quality polysaccharides.

Introduction of Polysaccharides

Along with nucleic acids and proteins, polysaccharides, are one of three classes of biopolymers that exist ubiquitously in nature. Structurally, polysaccharides are biomacromolecules, in which monosaccharide units are joined together by O-glycosidic linkages. The O-glycosidic linkage is formed by the condensation or dehydration reaction of the hemiacetal hydroxyl group of one sugar (glycosyl donor) and a hydroxyl group of another sugar unit (glycosyl acceptor). Building blocks can be single sugars (acids) or multiple sugars (acids). Compared to proteins and nucleic acids whose primary structures are simply defined by types and consequences of monomers, the primary structures of polysaccharides vary in composition, sequence, regio- and stereo-types of linkages, branching, and molecular weight. The vast diversity of possible polysaccharides and their corresponding properties offer an almost unlimited source of biobased gel-forming materials. Particularly, viscoelastic and biological properties are often critical in medical applications.

Chemical Synthesis of Polysaccharides

There are generally three strategies are used to synthesize polysaccharides, including step-wise glycosylation, condensation polymerization, and ring-opening polymerization. However, in contrast to nucleic acids and proteins, whose synthesis can be efficiently achieved by commercial automated synthesizers, chemical synthesis of polysaccharides with well-defined structures remains difficult. The main difficulties lie in controlling the regioselectivity of multiple hydroxyl groups with similar reactivity, controlling the stereochemistry of the glycosidic linkages, and obtaining polysaccharides with high molecular weight. Despite these ongoing challenges, significant progress has been made for the chemical synthesis of natural and unnatural polysaccharides. There are two methods often used in the chemical synthesis: 1) polycondensation of tritylated sugar cyanoethylidene derivatives, which is used to synthesize stereoregular homopolysaccharides and regular heteropolysaccharides from oligosaccharide monomers; 2) ring-opening polymerization of anhydrosugars, which enables the synthesis of high molecular weight (1→6)-glycopyranans and (1→5)-glycofuranans, as well as random heteropolysaccharides.

Custom Polysaccharides Synthesis at Creative Biolabs

Structure-function relationships, such as linking the chemical structure of polysaccharides with materials properties will increasingly inform design and synthesis of polysaccharides. Equipped with world-leading technology platforms and professional scientific staff, Creative Biolabs has accumulated rich experience in the design and synthesis of polysaccharides. Our scientists have employed several powerful strategies for polysaccharide synthesis.

Various polysaccharides, such as linear polysaccharides, branched polysaccharides, hyperbranched polysaccharides, non-O-glycosidic linked polysaccharidemimetics, as well as pseudopolysaccharides derived from non-carbohydrate sources, have been successfully achieved. Our polysaccharide list contains items including but not limited to:

Polysaccharides with different functions, such as amine polysaccharide, thiol polysaccharide, and carboxyl polysaccharide.
Polysaccharides with different structures, such as alginate, cellulose, chitosan, dextran, and xylan.
Polysaccharides with different labels, such as fluorescein, biotin, near-Infrared or rhodamine.

Polysaccharides will revolutionize medical applications by creating functionalized and responsive material. The synthesis of custom polysaccharides will open a new biomaterial world. Enriched with experience and state-of-the-art facilities, Creative Biolabs offers top-quality service for polysaccharide synthesis to facilitate our clients’ project development. For more detailed information, please feel free to contact us or directly send us an inquiry.

Published data

Glycosaminoglycans (GAGs) are a class of long-chain, negatively charged polysaccharides whose biosynthesis involves the stepwise transfer of monosaccharide units from uridine diphosphate (UDP) sugar donors to sugar acceptors. Based on their structural characteristics, GAGs are divided into several types, including hyaluronic acid, chondroitin sulfate, heparin (HS), etc. HS is a special glycosaminoglycan that is widely distributed on the cell surface and in the extracellular matrix. It is composed of repeated disaccharide units and exhibits diverse biological activities through sulfation modification. In this study, the authors proposed a chemical method for the efficient synthesis of 4-thiol-N-acetyl-D-glucosamine uridine diphosphate (UDP-4-SH-GlcNAc) and directly incorporated sugars from this non-natural donor into HS through polysaccharide synthase. UDP-4-SH-GlcNAc not only served as a glycosyl donor, but also enabled the resulting 4-SH-GlcNAc residue to act as an acceptor, further participating in the polymerization reaction to form thioglycosidic bonds. This study reported the synthesis of sulfur-linked polysaccharides for the first time. Based on this result, thiol-modified nucleotide sugars might be used to prepare more complex sulfur-linked GAG analogs in the future.

Fig.1 Synthesis scheme of sulfo-4-thio-HS analogs. Fig.1 Synthesis process of sulfo-4-thio-HS analogs.¹

FAQ

Q1: How do you control regioselectivity during polysaccharide synthesis?

A1: Regioselectivity control is critical due to the presence of multiple hydroxyl groups with similar reactivity on the monosaccharide unit. We utilize a protecting group strategy to mask specific hydroxyl groups during the glycosylation step. This allows us to direct the formation of glycosidic bonds at specific positions. By systematically applying and removing protecting groups, we ensure precise control over the structure of the polysaccharide.

Q2: What are the common challenges in the chemical synthesis of polysaccharides?

A2: Common challenges include controlling the regio- and stereoselectivity of glycosidic bonds, achieving high molecular weights, and ensuring uniformity of the polysaccharide structure. Inconsistent reactions and purification difficulties also pose practical problems. Our team addresses these challenges by optimizing reaction conditions, using specific protecting groups, and employing advanced analytical methods for structural verification.

Q3: Can you synthesize polysaccharides with specific functional groups such as amines or thiols?

A3: Yes, we functionalize polysaccharides with a variety of groups, including amines, thiols, and carboxyls, which is achieved by incorporating monosaccharide units containing these groups or by modifying existing polysaccharides after synthesis through specific chemical reactions. Functionalized polysaccharides are crucial for targeted applications in biomedicine and materials science.

Customer Review

Preparation of custom polysaccharide materials
“We worked with Creative Biolabs to customize the synthesis of a polysaccharide complex with a unique branched structure for cancer drug delivery systems. The team demonstrated outstanding expertise in the design and synthesis process and customized the generated polysaccharides according to our specific needs to have excellent biocompatibility and targeting. We have made significant progress in our project, and the resulting polysaccharide material has shown excellent drug release performance in in vivo experiments.”

Precise Control of Polysaccharide Regioselectivity and Stereochemistry
“We have recently benefited greatly from the custom polysaccharide synthesis service performed by Creative Biolabs. Not only was the team able to precisely control the polysaccharide regioselectivity and stereochemistry, but they also provided a thorough analytical report. The resulting high molecular weight polysaccharide was highly effective and greatly advanced our research project.”

Reference

He, Peng, et al. "Chemoenzymatic synthesis of sulfur-linked sugar polymers as heparanase inhibitors." Nature Communications 13.1 (2022): 7438. Distributed under Open Access license CC BY 4.0, without modification.

For Research Use Only.