Please use this identifier to cite or link to this item: http://dx.doi.org/10.14279/depositonce-6833
Main Title: Construction of a polyproline structure with hydrophobic exterior using octahydroindole-2-carboxylic acid
Author(s): Kubyshkin, Vladimir
Budisa, Nediljko
Type: Article
Language Code: en
Abstract: The proline analogue (2S,3aS,7aS)-octahydroindole-2-carboxylic acid (Oic) has been previously applied as a proline substitute in pharmocologically active peptides and as a structural component of the antihypertensive drug Perindopril. Herein, we describe the formation of an oligoproline structure by an Oic oligomer. A series of Oic oligomers were investigated to show the structural and energetic contribution of appended residues to the structure. NMR investigation of these oligomers revealed an all-trans amide bond structure, and we provide evidence that a cascade-like mechanism is responsible for the all-trans folding cooperativity. X-ray crystallography of the Oic-hexapeptide clearly demonstrates that the all-trans structure of the Oic oligomer is a polyproline II helix. Thus, as a hydrophobic proline analog with a highly stable trans-amide bond, Oic represents an ideal building block for hydrophobic sites of polyproline II structures in biologically relevant contexts.
URI: https://depositonce.tu-berlin.de//handle/11303/7643
http://dx.doi.org/10.14279/depositonce-6833
Issue Date: 2016
Date Available: 19-Apr-2018
DDC Class: 540 Chemie und zugeordnete Wissenschaften
Sponsor/Funder: DFG, FOR 1805, Einfluss der Ribosomendynamik auf Regulation der Geschwindigkeit und Genauigkeit der Translation
License: https://creativecommons.org/licenses/by/3.0/
Journal Title: Organic & Biomolecular Chemistry
Publisher: Royal Society of Chemistry (RSC)
Publisher Place: Cambridge
Volume: 15
Issue: 3
Publisher DOI: 10.1039/c6ob02306a
Page Start: 619
Page End: 627
EISSN: 1477-0539
ISSN: 1477-0520
Appears in Collections:FG Biokatalyse » Publications

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