Chemoselective and microwave-assisted synthesis of glycopeptoids.
The chemoselective glycosylation of N-alkylaminooxy side chains with unprotected reducing sugars has proven useful for the synthesis of glycopeptides. Herein, we extend the N-alkylaminooxy strategy to the synthesis of glycopeptoids. A N-methylaminooxy submonomer was efficiently synthesized and incorporated into peptoids. Glycosylation of the peptoids proceeded chemoselectively and site-specifically at the N-methylaminooxy moieties. Employing microwave irradiation significantly increased the degree of glycosylation and shortened the reaction times.
Seo
Jiwon
J
Department of Bioengineering, Stanford University, 318 Campus Drive, Stanford, California 94305-5440, USA.
Michaelian
Nairie
N
Owens
Shawn C
SC
Dashner
Scott T
ST
Wong
Amanda J
AJ
Barron
Annelise E
AE
Carrasco
Michael R
MR
D006031:Glycosylation; D008872:Microwaves; D015394:Molecular Structure; D034444:Peptoids / Q000138:chemical synthesis* / Q000737:chemistry; D013237:Stereoisomerism
D034444:Peptoids