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Synthesis of O ‐(α‐Glyco)peptides by the N ‐Iodosuccinimide Procedure

1987; Wiley; Volume: 26; Issue: 9 Linguagem: Inglês

10.1002/anie.198708881

1521-3773

Horst Kessler, Matthias Kottenhahn, Andreas Kling, Čenêǩ Kolář,

Chemical Synthesis and Analysis

The glycosylation of serine or threonine in (protected) peptides can be accomplished by reaction with glycals and N-iodosuccinimide. The 2-iodo derivatives are obtained in high yields and with high diastereoselectivity. These derivatives can be converted into 2-deoxy-α-glycopeptides of the type 1 (R1, R2  H, OAc; R3  H, Me; X, Y  protecting groups, amino acid derivatives, or peptide derivatives).