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Synthesis and Placental Binding Potencies of Photosensitive Analogues of Luteinizing Hormone Releasing Hormone (LHRH) with Agonistic and Antagonistic Structures

1987; Wiley; Volume: 70; Issue: 2 Linguagem: Inglês

10.1002/hlca.19870700221

1522-2675

Z Maćkiewicz, Serge Bélisle, Diégo Bellabarba, Nicole Gallo‐Payet, Jean‐Guy Lehoux, Ginette Lagacé, Emanuel Escher,

Fluorine in Organic Chemistry

Abstract The synthesis of new photolabeling analogues of luteinizing hormone releasing hormone is described. Peptides were prepared by the solid‐phase method, and the photolabeling moiety was introduced as the 4′‐nitrophenyl‐alanine precursor. This amino acid, either of the L or D configuration, was placed at different positions and was modified afterwards to 4′‐azidophenylalanine. Structures with agonistic or antagonistic character were prepared, together with a peptide containing simultaneously the photolabeling moiety and a biotin substituent for future receptor isolations. Binding studies on placental and pituitary membranes indicate that these compounds represent promising candidates for receptor labeling studies.