Analogues of luteinizing hormone-releasing hormone (LH-RH) containing dehydroalanine in 6th position.
(Phe5, delta Ala6)-LH-RH and des-Gly10(Phe5, delta Ala6)-LH-RH ethylamide, two analogues of luteinizing hormone-releasing hormone (LH-RH), have been synthesised using fragment condensation approach in solution phase with minimum protection of the side chains. The presence of dehydroalanine in peptide fragments was confirmed by 1H n.m.r. and chemical analysis. Both the analogues were found to be inactive in comparison to LH-RH, indicating that alpha,beta-dehydrogenation of alanine in 6th position is not tolerated and suggesting that flexibility at this position may be crucial for the retention of biological activity.
Sharma
A K
AK
Department of Chemistry, University of Delhi, India.
Chauhan
V S
VS
D000409:Alanine / Q000031:analogs & derivatives; D006063:Chorionic Gonadotropin / Q000378:metabolism; D005260:Female; D007987:Gonadotropin-Releasing Hormone / Q000031:analogs & derivatives* / Q000138:chemical synthesis / Q000494:pharmacology; D006801:Humans; D007202:Indicators and Reagents; D010920:Placenta / Q000187:drug effects / Q000378:metabolism; D011247:Pregnancy; D011487:Protein Conformation; D013329:Structure-Activity Relationship
D006063:Chorionic Gonadotropin; D007202:Indicators and Reagents; C055804:LHRH, Phe(5)-delta-Ala(6)-; C055805:LHRH, Phe(5)-delta-Ala(6)-N-Et-ProNH2(9)-; D007987:Gonadotropin-Releasing Hormone; C015102:dehydroalanine; D000409:Alanine