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  • Title: Stereoselective synthesis of conformationally constrained glycosylated amino acids using an enzyme-catalyzed desymmetrization.
    Author: Lane JW, Halcomb RL.
    Journal: J Org Chem; 2003 Feb 21; 68(4):1348-57. PubMed ID: 12585874.
    Abstract:
    As part of an effort to probe the mechanism by which glycosyltransferases recognize glycoproteins and assemble the core structures of O-linked oligosaccharides, constrained glycopeptides, compounds 2 and 3, based on the alpha-N-acetylgalactosaminyl serine substructure 1, were designed. In this paper we describe a stereoselective preparation of protected versions of these compounds. A pig liver esterase-catalyzed enzymatic desymmetrization of a diacetate substrate, 10, was employed as a key component in the synthesis.
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