Journal
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY
Volume 128, Issue 46, Pages 15026-15033Publisher
AMER CHEMICAL SOC
DOI: 10.1021/ja065601q
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Funding
- NIGMS NIH HHS [GM 073500-02] Funding Source: Medline
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A novel method for the synthesis of N-linked glycopeptides using the sugar-assisted ligation strategy from cysteine free peptides is presented. The ligation junction tolerates a variety of amino acids, favoring less hindered amino acids and those with side chains that could serve as a general base in the ligation pathway. Since our approach allows the ligation of difficult junctions, the method could be applied to the synthesis of large peptides by enzymatic removal of the sugar moiety. Alternatively, more complex glycopeptides can be synthesized using glycosyltransferases. Together, this sequence of reactions should be amenable to the synthesis of glycopeptides and glycoproteins and their deglycosylated products.
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