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:
Notes: --- - "Cited By (since 1996): 6" - "Export Date: 17 November 2011" - "CODEN: JACSA" - "Source: Scopus"
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  1. David Y Gin
    41 Gin
  2. Daniel A. Ryan
    2 Ryan