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

Kessler Horst | Zendy; Kottenhahn Matthias | Zendy; Kling Andreas | Zendy; Kolar Cenek | Zendy

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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).

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