Studies on the synthesis of cyclic pentapeptides as LHRH antagonists and the factors that influence cyclization yield

Six cyclic pentapeptides containing two or three non‐protein amino acids have been synthesized by cyclization of linear precursors in dilute solution and characterized by TLC, HPLC, NMR, melting point, specific rotation etc. A total of 72 cyclization reactions were carried out to study the factors t...

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Bibliographic Details
Published in:Journal of peptide science 2002-08, Vol.8 (8), p.418-430
Main Authors: Gao, Xing-Ming, Ye, Yun-Hua, Bernd, Michael, Kutscher, Bernhard
Format: Article
Language:English
Subjects:
2-chlorotrityl chloride resin
Amino Acid Sequence
Chromatography, High Pressure Liquid
Chromatography, Thin Layer
coupling reagent
cyclic pentapeptide
cyclization
Gonadotropin-Releasing Hormone - antagonists & inhibitors
Indicators and Reagents
LHRH antagonist
Nuclear Magnetic Resonance, Biomolecular
Oligopeptides - chemical synthesis
Oligopeptides - chemistry
Oligopeptides - pharmacology
Peptides, Cyclic - chemical synthesis
Peptides, Cyclic - chemistry
Peptides, Cyclic - pharmacology
Spectrometry, Mass, Electrospray Ionization
Spectrometry, Mass, Fast Atom Bombardment
Temperature
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Summary:Six cyclic pentapeptides containing two or three non‐protein amino acids have been synthesized by cyclization of linear precursors in dilute solution and characterized by TLC, HPLC, NMR, melting point, specific rotation etc. A total of 72 cyclization reactions were carried out to study the factors that influence head‐to‐tail cyclization: linear precursor sequence, coupling reagent, residue configuration, the proportion of DMAP additive, concentration, reaction temperature and reaction time. The cyclic pentapeptides will be modified by active moieties and evaluated as LHRH antagonists. Copyright © 2002 European Peptide Society and John Wiley & Sons, Ltd.
ISSN:1075-2617
1099-1387
DOI:10.1002/psc.397