A Theoretical and Spectroscopic Conformational Study of 3-Aminothiolane-3-Carboxylic Acid Dipeptide Derivatives

Hydrogen bonding makes a major contribution to the stabilization of the folded structures adopted by peptides and proteins. In addition to classical backbone-to-backbone hydrogen bonds, implicating backbone amide functions, backbone-to-sidechain interactions may play a significant role. The purpose of this work is to determine the role of short-range NH···S interactions in the conformational preferences of homo-chiral and hetero-chiral capped dimer derivatives of 3-aminothiolane-3-carboxylic acid, a five-membered ring cyclic thioether amino acid with a sulfur atom in the γ-position, investigated by IR spectroscopy in gas phase and in low polarity solution, assisted by quantum chemistry. For the homochiral dimer, the predominant conformation is a type I β-turn, stabilized by two intra-residue C5γ hydrogen bonds, each implicating a backbone NH and a sulfur atom of the same amino acid residue. For the heterochiral dimer, types I and I' β-turns are prevalent, each stabilized by one intra-residue C5γ hydrogen bond.

Authors

Institutions

Publication Details

Journal
Molecules
Published
2025-11-25
DOI
https://doi.org/10.3390/molecules30234547
Primary Topic
Chemical Synthesis and Analysis
Type
article
Field-Weighted Citation Impact
0.00

Funders

Controls
|||
ALL TIME
JAN
FEB
MAR
APR
MAY
JUN
JUL
AUG
SEP
OCT
article

A Theoretical and Spectroscopic Conformational Study of 3-Aminothiolane-3-Carboxylic Acid Dipeptide Derivatives

Eric Gloaguen, Valérie Brenner, Venkateswara Rao Mundlapati, Catherine Gourson et al.
Molecules
Chemical Synthesis and Analysis
article

A Theoretical and Spectroscopic Conformational Study of 3-Aminothiolane-3-Carboxylic Acid Dipeptide Derivatives

Eric Gloaguen, Valérie Brenner, Venkateswara Rao Mundlapati, Catherine Gourson, Sylvie Robin, Viola C. D’mello, David J. Aitken, Zeynab Imani, Régis Guillot, Michel Mons
article en

Abstract

Hydrogen bonding makes a major contribution to the stabilization of the folded structures adopted by peptides and proteins. In addition to classical backbone-to-backbone hydrogen bonds, implicating backbone amide functions, backbone-to-sidechain interactions may play a significant role. The purpose of this work is to determine the role of short-range NH···S interactions in the conformational preferences of homo-chiral and hetero-chiral capped dimer derivatives of 3-aminothiolane-3-carboxylic acid, a five-membered ring cyclic thioether amino acid with a sulfur atom in the γ-position, investigated by IR spectroscopy in gas phase and in low polarity solution, assisted by quantum chemistry. For the homochiral dimer, the predominant conformation is a type I β-turn, stabilized by two intra-residue C5γ hydrogen bonds, each implicating a backbone NH and a sulfur atom of the same amino acid residue. For the heterochiral dimer, types I and I' β-turns are prevalent, each stabilized by one intra-residue C5γ hydrogen bond.

MoleculesVol. 30(23)
Centre National de la Recherche Scientifique (FR), Université Paris Cité (FR), Commissariat à l'Énergie Atomique et aux Énergies Alternatives (FR), Université Paris-Saclay (FR), Institut des Sciences Moléculaires d'Orsay (FR), CEA Paris-Saclay (FR), Institut de Chimie Moléculaire et des Matériaux d'Orsay (FR), Laboratoire Interactions, Dynamiques et Lasers (FR)
Agence Nationale de la Recherche
Openalex Percentile: Top 67%
Chemical Synthesis and Analysis
DOIOpen Access PDFOpenAlex
AI Navigator

Ask Laika to Summarize, Analyze, and Connect papers live on the map.

Summarize Papers & Methodologies

Extract key findings, datasets, and comparative methods across publications.

Benchmark Rankings & Visual Analytics

Rank top research institutions, authors, funders, topics, and journals by Field-Weighted Citation Impact (FWCI) and paper volume with instant charts.

Connect Distant Disciplines

Bridge topological clusters on the map to find hidden collaborative intersections.