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Synthesis of O ‐(α‐Glyco)peptides by the N ‐Iodosuccinimide Procedure
Author(s) -
Kessler Horst,
Kottenhahn Matthias,
Kling Andreas,
Kolar Cenek
Publication year - 1987
Publication title -
angewandte chemie international edition in english
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 5.831
H-Index - 550
eISSN - 1521-3773
pISSN - 0570-0833
DOI - 10.1002/anie.198708881
Subject(s) - glycopeptide , serine , threonine , chemistry , glycosylation , peptide , protecting group , amino acid , cyclic peptide , combinatorial chemistry , stereochemistry , organic chemistry , biochemistry , alkyl , antibiotics , enzyme
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 (R 1 , R 2 H, OAc; R 3 H, Me; X, Y protecting groups, amino acid derivatives, or peptide derivatives).