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 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.
Gao
Xing-Ming
XM
Key Laboratory of Bioorganic Chemistry and Molecular Engineering, Ministry of Education, Department of Chemistry, Peking University, Beijing, China
Ye
Yun-Hua
YH
Bernd
Michael
M
Kutscher
Bernhard
B
D000595:Amino Acid Sequence; D002851:Chromatography, High Pressure Liquid; D002855:Chromatography, Thin Layer; D007987:Gonadotropin-Releasing Hormone / Q000037:antagonists & inhibitors*; D007202:Indicators and Reagents; D019906:Nuclear Magnetic Resonance, Biomolecular; D009842:Oligopeptides / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology*; D010456:Peptides, Cyclic / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology*; D021241:Spectrometry, Mass, Electrospray Ionization; D016339:Spectrometry, Mass, Fast Atom Bombardment; D013696:Temperature
D007202:Indicators and Reagents; D009842:Oligopeptides; D010456:Peptides, Cyclic; D007987:Gonadotropin-Releasing Hormone