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1. Preparation of S‐ and N‐Linked Glycosylated Amino Acid Building Blocks for Solid‐phase Glycopeptide Library Synthesis*

Author

Selene van der Poel, C.E.P. Maljaars, Johannis P. Kamerling, Wim de Oude, Niels J. M. Pijnenburg, and Koen M. Halkes

Subjects
chemistry.chemical_classification, chemistry.chemical_compound, chemistry, Stereochemistry, Phase (matter), Yield (chemistry), Organic Chemistry, Glycosyl, Biochemistry, Combinatorial chemistry, Glycopeptide, Amino acid
Abstract

A general route for the preparation of 1,2‐trans‐linked S‐glycosylated amino acid building blocks by a Lewis‐acid‐promoted condensation of peracetylated glycosyl donors and N α‐Fmoc‐Cys‐OH, in good overall yield, is described. In addition, a short and time‐efficient route was applied for the synthesis of N‐glycosylated amino acid building blocks in good overall yields by coupling unprotected glycosylamines and N α‐Fmoc‐Asp(OH)‐O t Bu using TBTU activation. * In memory of Professor Jacques H. van Boom.

Published
2005
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