Synthesis of O-glycopeptides
The Necessity of Glycopeptide Synthesis
Glycopeptides present vital roles in multiple physiological processes, such as cell growth, cell differentiation, and cell adhesion. To better understand the structure-activity relationships (SARs) and functions, the glycopeptides with specific structures are required. However, the microheterogeneity at carbohydrate portions and uncontrollable glycosylation in the biosynthetic approach largely restrict their access and sources. In this case, it is urgent to develop efficient synthetic approaches for the preparation of pure and structurally well-defined glycopeptides.
SPGPS Technology for O-glycopeptides Synthesis
O-glycosylation is an important protein modification type to affect a series of biological functions and immunity. Based on the building block approach, solid-phase O-glycopeptide synthesis (SPGPS) is the most effective method to obtain glycosylated peptides with different sugar moieties on different amino acid side chains. Among them, the development of convenient glycosylation building block synthesis pathways and effective glycopeptide solid-phase synthesis pathways are crucial. The SPGPS technology has been also used for the construction of glycopeptide microarray chips for drug discovery.
SHGPFT Technology for O-glycopeptides Synthesis
In recent decades, solid-phase peptide synthesis (SPPS) has been well applied, especially using glycosylated amino acids or oligosaccharides as building blocks. But it is often cumbersome to operate and low efficiency. By combining solid-phase glycosylation and light fluoroglycan donor schemes, solid-phase hybrid glycopeptide ion procedure and the fluorous tagging method (SHGPFT) is a novel solid-phase synthesis method for the preparation of O-linked glycopeptides. Based on the SHGPFT approach, the pentapeptide with a monosaccharide motif has been synthesized.
Advantages of SHGPFT
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The F-tag of the fluorous phase in the SHGPFT protocol greatly simplifies the purification procedure and also avoids impurities due to incomplete coupling.
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The stable aryl hydrazine linker presents acidic and/or basic liability to the glycol moiety and side-protection groups of glycopeptides so that eliminates the risk to destroy the glycopeptides’ structure.
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This SHGPFT method has wide applicability for glycopeptide synthesis.
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This SHGPFT method makes it possible to construct a pure glycopeptide library with a defined structure.
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The pure desired product can be obtained by simple fluorous solid-phase extraction (F-SPE) because only the final target glycopeptide contains F-tag.
Creative Biolabs has been a long-term expert in the field of glycomics. As a pioneer and the undisrupted global leader in glycan research, we offer a variety of products and services including custom glycoprotein synthesis. If you are interested in our products or services, please do not hesitate to contact us for more detailed information.
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