Non-covalent interactions reveal the protein chain δ conformation in a flexible single-residue model

被引：4

作者：

Imani, Zeynab ^{[1
,5
]}

Mundlapati, Venkateswara Rao ^{[2
,6
]}

Brenner, Valerie ^{[2
]}

Gloaguen, Eric ^{[2
]}

Le Barbu-Debus, Katia ^{[3
]}

Zehnacker-Rentien, Anne ^{[3
]}

Robin, Sylvie ^{[1
,4
]}

Aitken, David J. ^{[1
]}

Mons, Michel ^{[2
]}

机构：

[1] Univ Paris Saclay, ICMMO, CNRS, F-91400 Orsay, France

[2] Univ Paris Saclay, LIDYL, CNRS, CEA, F-91191 Gif Sur Yvette, France

[3] Univ Paris Saclay, ISMO, CNRS, F-91400 Orsay, France

[4] Univ Paris, Fac Pharm, F-75006 Paris, France

[5] Univ Montreal, Dept Chim, Montreal, PQ, Canada

[6] Univ Toulouse, Inst Rech Astrophys & Planetol, Toulouse, France

来源：

CHEMICAL COMMUNICATIONS | 2023年 / 59卷 / 09期

关键词：

HYDROGEN-BOND; INTRAMOLECULAR CATALYSIS;

D O I：

10.1039/d2cc06658k

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

The delta conformation is a local secondary structure in proteins that implicates a pi(amide) N-HMIDLINE HORIZONTAL ELLIPSISN interaction between a backbone N atom and the NH of the following residue. Small-molecule models thereof have been limited so far to rigid proline-type compounds. We show here that in derivatives of a cyclic amino acid with a sulphur atom in the gamma-position, specific side-chain/backbone N-HMIDLINE HORIZONTAL ELLIPSISS interactions stabilize the delta conformation sufficiently to allow it to compete with classical C5 and C7 H-bonded conformers.

引用

页码：1161 / 1164

页数：4

共 35 条

[1] Evidence of an Unusual N-H•••N Hydrogen Bond in Proteins [J].

Adhikary, Ramkrishna ;

Zimmermann, Joerg ;

Liu, Jian ;

Forrest, Ryan P. ;

Janicki, Tesia D. ;

Dawson, Philip E. ;

Corcelli, Steven A. ;

Romesberg, Floyd E. .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2014, 136 (39) :13474-13477

[2] Aib residues in peptaibiotics and synthetic sequences: Analysis of nonhelical conformations [J].

Aravinda, Subrayashastry ;

Shamala, Narayanaswamy ;

Balaram, Padmanabhan .

CHEMISTRY & BIODIVERSITY, 2008, 5 (07) :1238-1262

[3]

Bartlett GJ, 2010, NAT CHEM BIOL, V6, P615, DOI [10.1038/nchembio.406, 10.1038/NCHEMBIO.406]

[4] Stabilization of Azapeptides by Namide•••H-Namide Hydrogen Bonds [J].

Baruah, Kalpita ;

Sahariah, Biswajit ;

Sakpal, Sushil S. ;

Deka, Jugal Kishore Rai ;

Bar, Arun Kumar ;

Bagchi, Sayan ;

Sarma, Bani Kanta .

ORGANIC LETTERS, 2021, 23 (13) :4949-4954

[5] Identification of the intrinsic conformational properties of 1-aminocyclobutane-1-carboxylic acid [J].

Casanovas, Jordi ;

Zanuy, David ;

Nussinov, Ruth ;

Aleman, Carlos .

CHEMICAL PHYSICS LETTERS, 2006, 429 (4-6) :558-562

[6] Intramolecular catalysis of amide isomerization [J].

Cox, C ;

Young, VG ;

Lectka, T .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1997, 119 (09) :2307-2308

[7] Intramolecular catalysis of amide isomerization:: Kinetic consequences of the 5-NH- -Na hydrogen bond in prolyl peptides [J].

Cox, C ;

Lectka, T .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1998, 120 (41) :10660-10668

[8] Characterization of Asx Turn Types and Their Connate Relationship with β-Turns [J].

D'mello, Viola C. ;

Goldsztejn, Gildas ;

Mundlapati, Venkateswara Rao ;

Brenner, Valerie ;

Gloaguen, Eric ;

Charnay-Pouget, Florence ;

Aitken, David J. ;

Mons, Michel .

CHEMISTRY-A EUROPEAN JOURNAL, 2022, 28 (25)

[9] Unconventional N-H ••• N Hydrogen Bonds Involving Proline Backbone Nitrogen in Protein Structures [J].

Deepak, R. N. V. Krishna ;

Sankararamakrishnan, Ramasubbu .

BIOPHYSICAL JOURNAL, 2016, 110 (09) :1967-1979

[10] THE OCCURRENCE OF C-H-CENTER-DOT-CENTER-DOT-CENTER-DOT-O HYDROGEN-BONDS IN PROTEINS [J].

DEREWENDA, ZS ;

LEE, L ;

DEREWENDA, U .

JOURNAL OF MOLECULAR BIOLOGY, 1995, 252 (02) :248-262

← 1 2 3 4 →