1207719-13-8Relevant articles and documents
Structure-activity analysis of the growth hormone secretagogue GHRP-6 by α- And β-Amino γ-lactam positional scanning
Boutard, Nicolas,Jamieson, Andrew G.,Ong, Huy,Lubell, William D.
scheme or table, p. 40 - 50 (2010/10/21)
Incorporation of amino lactams into biologically active peptides restricts conformational mobility and may enhance selectivity and increase potency. α- and β-amino γ-lactams (Agl and Bgl), in both S and R configurations, were introduced into the growth hormone secretagogue GHRP-6 using a Fmoc-compatible solid-phase protocol relying on N-alkylation with five- and six-membered cyclic sulfamidates, followed by lactam annulation under microwave heating. Using this protocol in conjunction with IRORI Kan TM techniques furnished eleven new GHRP-6 analogs, and their binding affinity IC50 values on both the growth hormone secretagogue receptor 1a (GHS-R1a) and CD36 receptors are herein reported. The results indicate that selectivity towards one receptor or the other can be modulated by lactam substitution, typically at the Ala3 and the d-Phe5 positions.