Literature DB >> 21751326

An evaluation of peptide-bond isosteres.

Amit Choudhary1, Ronald T Raines.   

Abstract

Peptide-bond isosteres can enable a deep interrogation of the structure and function of a peptide or protein by amplifying or attenuating particular chemical properties. In this Minireview, the electronic, structural, and conformational attributes of four such isosteres-thioamides, esters, alkenes, and fluoroalkenes-are examined in detail. In particular, the ability of these isosteres to partake in noncovalent interactions is compared with that of the peptide bond. The consequential perturbations provide a useful tool for chemical biologists to reveal new structure-function relationships, and to endow peptides and proteins with desirable attributes.
Copyright © 2011 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim.

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Year:  2011        PMID： 21751326      PMCID： PMC3253576          DOI： 10.1002/cbic.201100272

Source DB:  PubMed          Journal:  Chembiochem        ISSN： 1439-4227            Impact factor:   3.164


  60 in total

1.  Thioxylation as One-Atom-Substitution Generates a Photoswitchable Element within the Peptide Backbone We thank Dr. Peter Bayer for the NMR investigations and Dirk Wildemann for his assistance with the peptide syntheses. This work was supported by the Deutsche Forschungsgemeinschaft, the Fond der Chemischen Industrie, the Boehringer-Ingelheim-Stiftung, and the Land Sachsen-Anhalt.

Authors: 
Journal:  Angew Chem Int Ed Engl       Date:  2000-03       Impact factor: 15.336

2.  Olefinic Peptide Nucleic Acids (OPAs): New Aspects of the Molecular Recognition of DNA by PNA The team at the University of Bern thanks the Swiss National Science Foundation and Novartis Pharma AG, Basel, for generous financial support.

Authors: 
Journal:  Angew Chem Int Ed Engl       Date:  2000-04       Impact factor: 15.336

3.  Methyl- and (Trifluoromethyl)alkene Peptide Isosteres: Synthesis and Evaluation of Their Potential as beta-Turn Promoters and Peptide Mimetics.

Authors:  Peter Wipf; Todd C. Henninger; Steven J. Geib
Journal:  J Org Chem       Date:  1998-09-04       Impact factor: 4.354

4.  Conformational stability of collagen relies on a stereoelectronic effect.

Authors:  L E Bretscher; C L Jenkins; K M Taylor; M L DeRider; R T Raines
Journal:  J Am Chem Soc       Date:  2001-01-31       Impact factor: 15.419

5.  Amide-to-ester substitution in coiled coils: the effect of removing hydrogen bonds on protein structure.

Authors:  Jessica A Scheike; Carsten Baldauf; Jan Spengler; Fernando Albericio; M Teresa Pisabarro; Beate Koksch
Journal:  Angew Chem Int Ed Engl       Date:  2007       Impact factor: 15.336

6.  Understanding the relative acyl-transfer reactivity of oxoesters and thioesters: computational analysis of transition state delocalization effects.

Authors:  W Yang; D G Drueckhammer
Journal:  J Am Chem Soc       Date:  2001-11-07       Impact factor: 15.419

7.  Electrostatic versus steric effects in peptidomimicry: synthesis and secondary structure analysis of gramicidin S analogues with (E)-alkene peptide isosteres.

Authors:  Jingbo Xiao; Bernard Weisblum; Peter Wipf
Journal:  J Am Chem Soc       Date:  2005-04-27       Impact factor: 15.419

8.  Collagen stability: insights from NMR spectroscopic and hybrid density functional computational investigations of the effect of electronegative substituents on prolyl ring conformations.

Authors:  Michele L DeRider; Steven J Wilkens; Michael J Waddell; Lynn E Bretscher; Frank Weinhold; Ronald T Raines; John L Markley
Journal:  J Am Chem Soc       Date:  2002-03-20       Impact factor: 15.419

9.  Amide-to-E-olefin versus amide-to-ester backbone H-bond perturbations: Evaluating the O-O repulsion for extracting H-bond energies.

Authors:  Yanwen Fu; Jianmin Gao; Jan Bieschke; Maria A Dendle; Jeffery W Kelly
Journal:  J Am Chem Soc       Date:  2006-12-20       Impact factor: 15.419

10.  Peptide bond mimicry by (E)-alkene and (Z)-fluoroalkene peptide isosteres: synthesis and bioevaluation of alpha-helical anti-HIV peptide analogues.

Authors:  Shinya Oishi; Hirotaka Kamitani; Yasuyo Kodera; Kentaro Watanabe; Kazuya Kobayashi; Tetsuo Narumi; Kenji Tomita; Hiroaki Ohno; Takeshi Naito; Eiichi Kodama; Masao Matsuoka; Nobutaka Fujii
Journal:  Org Biomol Chem       Date:  2009-06-04       Impact factor: 3.876
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  46 in total

Review 1.  Designing antimicrobial peptides: form follows function.

Authors:  Christopher D Fjell; Jan A Hiss; Robert E W Hancock; Gisbert Schneider
Journal:  Nat Rev Drug Discov       Date:  2011-12-16       Impact factor: 84.694

2.  Preparation and evaluation at the delta opioid receptor of a series of linear leu-enkephalin analogues obtained by systematic replacement of the amides.

Authors:  Kristina Rochon; Arnaud Proteau-Gagné; Philippe Bourassa; Jean-François Nadon; Jérome Côté; Véronique Bournival; Fernand Gobeil; Brigitte Guérin; Yves L Dory; Louis Gendron
Journal:  ACS Chem Neurosci       Date:  2013-05-20       Impact factor: 4.418

3.  Synthesis of thioester peptides for the incorporation of thioamides into proteins by native chemical ligation.

Authors:  Solongo Batjargal; Yun Huang; Yanxin J Wang; E James Petersson
Journal:  J Pept Sci       Date:  2014-01-09       Impact factor: 1.905

4.  Kinetic isotope effects support the twisted amide mechanism of Pin1 peptidyl-prolyl isomerase.

Authors:  Ana Y Mercedes-Camacho; Ashley B Mullins; Matthew D Mason; Guoyan G Xu; Brendan J Mahoney; Xingsheng Wang; Jeffrey W Peng; Felicia A Etzkorn
Journal:  Biochemistry       Date:  2013-10-24       Impact factor: 3.162

5.  Individual Ion Binding Sites in the K(+) Channel Play Distinct Roles in C-type Inactivation and in Recovery from Inactivation.

Authors:  Kimberly Matulef; Alvin W Annen; Jay C Nix; Francis I Valiyaveetil
Journal:  Structure       Date:  2016-04-14       Impact factor: 5.006

6.  Prolyl 4-Hydroxylase: Substrate Isosteres in Which an (E)- or (Z)-Alkene Replaces the Prolyl Peptide Bond.

Authors:  James D Vasta; Amit Choudhary; Katrina H Jensen; Nicholas A McGrath; Ronald T Raines
Journal:  Biochemistry       Date:  2016-12-21       Impact factor: 3.162

Review 7.  Amide Bond Bioisosteres: Strategies, Synthesis, and Successes.

Authors:  Shikha Kumari; Angelica V Carmona; Amit K Tiwari; Paul C Trippier
Journal:  J Med Chem       Date:  2020-08-04       Impact factor: 7.446

8.  Isomannide-based peptidomimetics as inhibitors for human tissue kallikreins 5 and 7.

Authors:  Jocelia P C Oliveira; Renato F Freitas; Leandro Silva de Melo; Thalita G Barros; Jorge A N Santos; Maria A Juliano; Sérgio Pinheiro; Michael Blaber; Luiz Juliano; Estela M F Muri; Luciano Puzer
Journal:  ACS Med Chem Lett       Date:  2013-12-06       Impact factor: 4.345

9.  E- or Z-Selective synthesis of 4-fluorovinyl-1,2,3-triazoles with fluorinated second-generation Julia-Kocienski reagents.

Authors:  Rakesh Kumar; Govindra Singh; Louis J Todaro; Lijia Yang; Barbara Zajc
Journal:  Org Biomol Chem       Date:  2015-02-07       Impact factor: 3.876

10.  Labeling proteins with fluorophore/thioamide Förster resonant energy transfer pairs by combining unnatural amino acid mutagenesis and native chemical ligation.

Authors:  Rebecca F Wissner; Solongo Batjargal; Colin M Fadzen; E James Petersson
Journal:  J Am Chem Soc       Date:  2013-04-17       Impact factor: 15.419
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