Custom Glycopeptide Synthesis Services

Creative Biolabs has accumulated extensive experience to offer a full range of custom glycopeptide synthesis service to meet our customer’s every special requirement. We have provided thousands of clients with high-quality custom service of N-, O-, C-, and S-linked glycopeptide synthesis. We are confident to make sure that our service can assist global clients to attain their satisfied consequences in the shortest possible time.

Strategies of Glycopeptide Synthesis

Currently, there are three strategies for a glycopeptide synthesis with an oligosaccharide side chain. The first most common strategy utilizes solid-phase peptide synthesis (SPPS) with pre-formed glycosyl amino acids. Because O-glycosidic and intersaccharidic linkages are relatively labile towards acid, so it is required to select proper protecting groups to block the functional groups on both the glycan and the peptide part. Besides, proper protecting groups are of importance for the solid-phase and solution-phase synthesis of glycopeptides. Furthermore, in order to synthesize glycopeptides with complex oligosaccharide side chains, the second strategy of glycopeptide chemical or chemoenzymatic synthesis has been developed. This method utilizes a glycosyl amino acid with a relatively simple saccharide side chain in the peptide assembly and then elaborate the glycopeptide chemically or chemoenzymatically to expand the glycan. The third strategy of glycopeptides synthesis is the direct peptide glycosylation. This method does not require the use of any glycosyl amino acids and attempts to reach the maximum convergence by establishing a complex glycodomain first and then incorporating it directly into a peptide setting.

Specialized Glycopeptide Synthesis Services at Creative Biolabs

Glycopeptides have important biological functions in organisms. Synthetic glycopeptides have a wide range of applications, which promote the development of life science research, drug development, biomedical applications, and other fields. Creative Biolabs provides specialized glycopeptide synthesis services to clients around the world.

Custom Glycopeptide Synthesis Services at Creative Biolabs

Experienced in the field of glycopeptide synthesis, Creative Biolabs is the leading commercial source of synthetic and well-defined glycopeptides containing monosaccharides or oligosaccharides. Glycans can be covalently attached to the hydroxyl oxygen of Ser or Thr (O-glycosylation), the amide nitrogen of Asn (N-glycosylation), and the indole C2 carbon of Trp through a C-C linkage (C-glycosylation). S-linked glycopeptides can also be synthesized using a convergent strategy.

We have offered our customers a large number of glycopeptide synthesis services, such as mucin and mucin-like fragments incorporating sialylation, hinge domain glycopeptides, N glycophorin A derivatives and antiproliferative factor. Our glycopeptide synthesis service can offer a unique frontier for research in glycobiology and proteomics as well as for drug discovery and development, drug delivery/targeting, diagnostics development and other biotechnological applications.

Highlights

• N-linked glycopeptide synthesis
• O-linked glycopeptide synthesis
• C-linked glycopeptide synthesis
• S-linked glycopeptide synthesis
• Glycopeptides containing monosaccharides, such as Ser/Thr (GlcNAc), Ser/Thr (GalNAc), Asn (GlcNAc), Ser (Xyl), Thr (Man), etc.
• Glycopeptides containing oligosaccharides, such as Ser/Thr (Gal-GalNAc), Ser/Thr (Neu-Gal-GalNAc), Asn (Fuc-GlcNAc), etc.
• Custom glycopeptide synthesis

Based on a variety of strategies, we are confident to offer the best glycopeptide synthesis services for customers all over the world with a competitive price. There is no doubt that our services will promote your project success in a shorter time. If you are interested in custom glycopeptide synthesis service, please don’t hesitate to contact us for more detail information.

Published data

Glycosylation is a common strategy that is widely applied in peptides and proteins to mimic important post-translational modifications. Currently, in the field of glycochemistry, glycosyl disulfides have been studied as glycosyl donors or as new ways to prepare glycoproteins. Disulfide bonds are flexible and can be used for chemically selective modification of peptides and proteins. Glycosylation of peptides through disulfide bonds is a method to mimic the structure of N-glycoproteins. In this study, the authors developed an effective method to synthesize disulfide-linked glycopeptides. They used glycosylsulfenyl hydrazine reagents to rapidly synthesize target glycopeptides and perform site-specific control of cysteine residues in the peptide chain through disulfide bonds. This disulfide bond-linked glycopeptide synthesis method was based on the specific reaction of cysteine residues with electrophilic thiol carbohydrates. This method was highly versatile, and using the glycosyl reagent, disulfide bond linkage of glycopeptides in the solution phase or fixed on solid support could be easily achieved. Moreover, during the synthesis process, there was no need to protect the amino acid side chains in the peptide, and no deprotection step was required. The reaction was compatible with aqueous solutions, providing new possibilities for protein glycosylation.

Fig.1 Preparation process of disulfide-linked glycopeptides.¹

FAQs

Q1: What protecting groups are used during SPPS to ensure the integrity of the glycopeptide?

A1: During SPPS, protecting groups such as tert-butyl (tBu) to protect hydroxyl groups and trityl (Trt) to protect thiol groups are used. These protecting groups are stable under the conditions used during peptide synthesis but can be selectively removed at the end of the synthesis. The choice of protecting group ensures that the labile glycosidic bond is preserved throughout the synthesis.

Q2: What are the main advantages of using LPPS over SPPS?

A2: LPPS offers several advantages, including greater flexibility and control over the synthesis process, making it easier to handle large-scale reactions and complex glycopeptide structures. LPPS also makes it easier to purify intermediates and is more effective for specific types of glycopeptides where the protecting group strategy is critical.

Q3: What quality control procedures do you use to ensure the purity and integrity of your synthesized glycopeptides?

A3: Quality control measures include mass spectrometry (MS) to verify molecular weight, high-performance liquid chromatography (HPLC) to assess purity, and nuclear magnetic resonance (NMR) spectroscopy to confirm the structure, which ensures that the synthesized glycopeptide product meets the requirements.

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Reference

1. Banisalman, Katreen AF, et al. "Chemoselective Solution-and Solid-Phase Synthesis of Disulfide-Linked Glycopeptides." The Journal of Organic Chemistry 87.21 (2022): 14026-14036. Distributed under Open Access license CC BY 4.0, without modification.

Related Services:

• Custom Glycan Synthesis
• Custom Glycoprotein Synthesis
• Oligosaccharide Library Development