Photosubstitution of cymantrenylalanine as a tool in peptide chemistry. Synthesis and biological activity of new GnRH analogs

Beyond its aromatic character and important hydrophobicity, cymantrenylalanine, a metallocenic amino-acid, can be easily photosubstituted with phosphine and phosphite ligands to readily yield new analogs with different hydrophobicity and steric hindrance. The incorporation of phosphine and phosphite...

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Bibliographic Details
Published inInternational journal of peptide and protein research Vol. 32; no. 1; p. 56
Main Authors Ricouart, A, Maes, P, Battmann, T, Kerdelhue, B, Tartar, A, Sergheraert, C
Format Journal Article
LanguageEnglish
Published Denmark 01.07.1988
Subjects
Alanine - analogs & derivatives
Animals
Female
Gonadotropin-Releasing Hormone - analogs & derivatives
Gonadotropin-Releasing Hormone - chemical synthesis
Gonadotropin-Releasing Hormone - pharmacology
In Vitro Techniques
Indicators and Reagents
Luteinizing Hormone - metabolism
Magnetic Resonance Spectroscopy
Manganese
Organometallic Compounds
Photochemistry
Pituitary Gland, Anterior - drug effects
Pituitary Gland, Anterior - metabolism
Rats
Rats, Inbred Strains
Spectrophotometry, Infrared
Structure-Activity Relationship
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Summary:Beyond its aromatic character and important hydrophobicity, cymantrenylalanine, a metallocenic amino-acid, can be easily photosubstituted with phosphine and phosphite ligands to readily yield new analogs with different hydrophobicity and steric hindrance. The incorporation of phosphine and phosphite ligands is described. As an illustration of the offered possibilities, the synthesis and the biological activity of two new GnRH analogs modified in position 6 are reported.
ISSN:0367-8377
DOI:10.1111/j.1399-3011.1988.tb00926.x