Stereoselective N-glycosylation by Staudinger ligation.
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]
He
Yi
Y
Departments of Chemistry and Biochemistry, University of Wisconsin-Madison, Madison, WI 53706, USA.
Hinklin
Ronald J
RJ
Chang
Jiyoung
J
Kiessling
Laura L
LL
D000577:Amides / Q000737:chemistry; D001216:Asparagine / Q000737:chemistry; D001386:Azides / Q000737:chemistry; D006001:Glycoconjugates / Q000138:chemical synthesis*; D006020:Glycopeptides / Q000138:chemical synthesis; D006031:Glycosylation; D013237:Stereoisomerism
D000577:Amides; D001386:Azides; D006001:Glycoconjugates; D006020:Glycopeptides; D001216:Asparagine