PMID: 8985785Dec 1, 1996Paper

Alanine scan and N-methyl amide derivatives of Ac-bombesin[7-14]. Development of a proposed binding conformation at the neuromedin B (NMB) and gastrin releasing peptide (GRP) receptors

International Journal of Peptide and Protein Research
D C HorwellN Suman-Chauhan

Abstract

Alanine and N-methylation scans together with molecular modelling were implemented in order to propose a binding conformation of the minimum active fragment of bombesin (BB), Ac-BB[7-14], to the gastrin releasing peptide (GRP) and neuromedin B (NMB) receptors. These data are also used to critically evaluate the previously proposed binding conformations such as alpha-helix and antiparallel beta-sheets. This shows that the previously reported conformations do not satisfy the experimental data. A new binding conformation of Ac-BB[7-14] is proposed consisting of three consecutive gamma-turns followed by a bend and finishing with two gamma-turns. This low energy conformation (analogous to a fragment of thymidylate synthase, 2TSC) of bombesin stabilized by five internal hydrogen bonds, and with the side chains of residues Trp8 and Leu13 held on the same side of the peptide, is in agreement with the experimentally observed data. This and the results of molecular modelling may aid in the synthesis of conformationally restricted high affinity bombesin analogues and/or high affinity template-based GRP or NMB receptor agonists and antagonists.

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Citations

Sep 6, 2002·Journal of Peptide Science : an Official Publication of the European Peptide Society·Dirk WeberHorst Kessler
Aug 13, 2020·Molecules : a Journal of Synthetic Chemistry and Natural Product Chemistry·Lisa-Maria RečnikThomas L Mindt
Oct 18, 2013·Journal of Peptide Science : an Official Publication of the European Peptide Society·Beatrice SeverinoElisa Perissutti
Nov 20, 2019·Journal of Peptide Science : an Official Publication of the European Peptide Society·Paul HoppenzAnnette G Beck-Sickinger
Dec 12, 2013·Journal of Labelled Compounds & Radiopharmaceuticals·Ibai E ValverdeThomas L Mindt
Jan 7, 2005·Journal of Peptide Science : an Official Publication of the European Peptide Society·Robert G BoyleKeiji Wada
Jan 5, 2002·Journal of Peptide Science : an Official Publication of the European Peptide Society·J G DarkerD Smart
Mar 20, 2009·The Journal of Physical Chemistry. B·Edyta Podstawka, Leonard M Proniewicz
Aug 27, 2015·Journal of Medicinal Chemistry·Ibai E ValverdeThomas L Mindt
May 25, 2002·The Journal of Organic Chemistry·Susana HerreroRosario Herranz

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