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Targeting Cysteine Thiols for in Vitro Site-specific Glycosylation of Recombinant Proteins
Published on: October 4, 2017
A general asymmetric synthesis of syn- and anti-beta-substituted cysteine and serine derivatives
Chiyi Xiong1, Wei Wang, Victor J Hruby
1Department of Chemistry, University of Arizona, Tucson, Arizona 85721, USA.
Abstract:
A stereodivergent synthetic route has been developed to make the optically pure anti- and syn-beta-substituted cysteine and serine derivatives. In this approach, the key intermediates, > 94% enantiomerically pure cyclic sulfates 3 and aziridines 7, were prepared from alpha,beta-unsaturated esters 1, employing the Sharpless asymmetric dihydroxylation. The high regio- and stereoselective ring-opening reactions of cyclic sulfates and aziridines provided enantiomerically pure beta-substituted cysteine and serine derivatives.
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