Analogues of luteinizing hormone-releasing hormone (LH-RH) containing dehydroalanine in 6th position

Chauhan, V. S. ; Sharma, Ashwani K. (1988) Analogues of luteinizing hormone-releasing hormone (LH-RH) containing dehydroalanine in 6th position International journal of peptide and protein research, 31 (2). pp. 225-230. ISSN 0367-8377

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Official URL: http://onlinelibrary.wiley.com/doi/10.1111/j.1399-...

Related URL: http://dx.doi.org/10.1111/j.1399-3011.1988.tb00027.x

Abstract

Phe5, ΔAla6)-LH-RH and des-Gly10(Phe5, Δ 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 1 H n.m.r. and chemical analysis. Both the analogues were found to be inactive in comparison to LH-RH, indicating that α , β -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.

Item Type:Article
Source:Copyright of this article belongs to Munksgaard International Publishers.
Keywords:Dehydroalanine; Fragment Condensation; Lh-rh Analogues; Minimal Protection Approach
ID Code:8205
Deposited On:26 Oct 2010 12:11
Last Modified:30 May 2011 11:48

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