Stereoselective N-Glycosylation by Staudinger Ligation
| Autor: | Laura L. Kiessling, Jiyoung Chang, Yi He, Ronald J. Hinklin |
|---|---|
| Rok vydání: | 2005 |
| Předmět: |
Azides
Glycosylation Stereochemistry Stereoisomerism Biochemistry Chemical synthesis chemistry.chemical_compound N-linked glycosylation Glycosyl Asparagine Physical and Theoretical Chemistry chemistry.chemical_classification Organic Chemistry Glycopeptides food and beverages General Medicine Amides Glycopeptide carbohydrates (lipids) chemistry lipids (amino acids peptides and proteins) Stereoselectivity Chemical ligation Glycoprotein Glycoconjugates |
| Zdroj: | ChemInform. 36 |
| ISSN: | 1522-2667 0931-7597 |
| DOI: | 10.1002/chin.200513217 |
| Popis: | Stereoselective methods for the chemical synthesis of beta-N-glycosyl amides are needed to generate glycopeptides and glycoproteins. Here, we report that the Staudinger ligation can be used to form glycosylated asparagine derivatives. The reaction proceeds with high stereoselectivity, and a variety of glycosyl azides can function as substrates. Our results provide precedence for the use of this powerful amide-bond-forming reaction for N-glycopeptide synthesis. [reaction: see text] |
| Databáze: | OpenAIRE |
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