Ring-opening of aziridine-2-carboxamides with carbohydrate C1-O-nucleophiles. Stereoselective preparation of α- and β-O-glycosyl serine conjugates Journal Article

   

Authors:	Ryan, D. A.; Gin, D. Y.
Article Title:	Ring-opening of aziridine-2-carboxamides with carbohydrate C1-O-nucleophiles. Stereoselective preparation of α- and β-O-glycosyl serine conjugates
Abstract:	The stereoselective formation of the α-GalNAc-Ser linkage via the ring opening of aziridine-2-carboxamides with pyranose C1-O-nucleophiles is described. The process is tolerant to the native C2-NHAc group, can be modulated to provide either the α- or β-glycoside through judicious choice of solvent and metal counterion, and is amenable to other classes of O-glycosyl-Ser constructs such as the β-GlcNAc-Ser and α-Man-Ser linkages. This coupling reaction also led to the development of the o-allylbenzyl (ABn) moiety as a new C-terminus carboxyl protective group, which allows for the use of novel methods for N- and C-terminus extension of amino acids following carbohydrate conjugation. Copyright © 2008 American Chemical Society.
Keywords:	unclassified drug; serine; carboxy terminal sequence; oxygen; protein synthesis; glycosylation; molecular structure; carbohydrates; carbohydrate; stereochemistry; stereoisomerism; protein glycosylation; ring opening; chlorine; alpha o glycosyl serine; aziridine 2 carboxamide; beta o glycosyl serine; serine derivative; aziridines
Journal Title:	Journal of the American Chemical Society
Volume:	130
Issue:	46
ISSN:	0002-7863
Publisher:	American Chemical Society
Date Published:	2008-11-19
Start Page:	15228
End Page:	15229
Language:	English
DOI:	10.1021/ja804589j
PUBMED:	18950157
PROVIDER:	scopus
PMCID:	PMC2648612
DOI/URL:	http://www.scopus.com/inward/record.url?eid=2-s2.0-56449098615&partnerID=40&md5=1880ce0fd31e87a2bfcf58d05c900ee0
Notes:	--- - "Cited By (since 1996): 6" - "Export Date: 17 November 2011" - "CODEN: JACSA" - "Source: Scopus"

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