title: Chemoselective and microwave-assisted synthesis of glycopeptoids.
abstract: 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.
authors.affiliation: Department of Bioengineering, Stanford University, 318 Campus Drive, Stanford, California 94305-5440, USA.
authors.forename: Jiwon
authors.initials: J
authors.lastname: Seo
authors.forename: Nairie
authors.initials: N
authors.lastname: Michaelian
authors.forename: Shawn C
authors.initials: SC
authors.lastname: Owens
authors.forename: Scott T
authors.initials: ST
authors.lastname: Dashner
authors.forename: Amanda J
authors.initials: AJ
authors.lastname: Wong
authors.forename: Annelise E
authors.initials: AE
authors.lastname: Barron
authors.forename: Michael R
authors.initials: MR
authors.lastname: Carrasco
mesh_terms: D006031:Glycosylation; D008872:Microwaves; D015394:Molecular Structure; D034444:Peptoids / Q000138:chemical synthesis* / Q000737:chemistry; D013237:Stereoisomerism
chemical_list: D034444:Peptoids