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On‐resin head‐to‐tail cyclization of cyclotetrapeptides: optimization of crucial parameters
Author(s) -
Alcaro Maria C.,
Sabatino Giuseppina,
Uziel Jacques,
Chelli Mario,
Ginanneschi Mauro,
Rovero Paolo,
Papini Anna M.
Publication year - 2004
Publication title -
journal of peptide science
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.475
H-Index - 66
eISSN - 1099-1387
pISSN - 1075-2617
DOI - 10.1002/psc.512
Subject(s) - side chain , chemistry , amino acid , sequence (biology) , combinatorial chemistry , ring (chemistry) , head (geology) , stereochemistry , biochemistry , organic chemistry , biology , polymer , paleontology
Cyclotetrapeptides are constrained cyclic peptides whose synthesis is considered a difficult task. A methodology based on on‐resin head‐to‐tail cyclization by anchoring the side chain of a trifunctional amino acid was investigated. A series of model cyclotetrapeptides containing the RGD sequence cyclo(Xaa‐Arg‐Gly‐Asp) (Xaa = Ala, Phe, Phg, D ‐Ala, D ‐Phe, D ‐Phg) was synthesized with no cyclodimerization by‐products. An evaluation and optimization study of all of the parameters directly involved in the ring closure was performed. Copyright © 2003 European Peptide Society and John Wiley & Sons, Ltd.