Literature DB >> 25967743

Thioamides in the collagen triple helix.

Robert W Newberry1, Brett VanVeller, Ronald T Raines.   

Abstract

To probe noncovalent interactions within the collagen triple helix, backbone amides were replaced with a thioamide isostere. This subtle substitution is the first in the collagen backbone that does not compromise thermostability. A triple helix with a thioamide as a hydrogen bond donor was found to be more stable than triple helices assembled from isomeric thiopeptides.

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Year:  2015        PMID： 25967743      PMCID： PMC4449287          DOI： 10.1039/c5cc02685g

Source DB:  PubMed          Journal:  Chem Commun (Camb)        ISSN： 1359-7345            Impact factor:   6.222


  43 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.  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

3.  Benzotriazole-assisted thioacylation.

Authors:  Alan R Katritzky; Rachel M Witek; Valerie Rodriguez-Garcia; Prabhu P Mohapatra; James W Rogers; Janet Cusido; Ashraf A A Abdel-Fattah; Peter J Steel
Journal:  J Org Chem       Date:  2005-09-30       Impact factor: 4.354

4.  Crystal and molecular structure of a collagen-like peptide at 1.9 A resolution.

Authors:  J Bella; M Eaton; B Brodsky; H M Berman
Journal:  Science       Date:  1994-10-07       Impact factor: 47.728

5.  Importance of ring puckering versus interstrand hydrogen bonds for the conformational stability of collagen.

Authors:  Roman S Erdmann; Helma Wennemers
Journal:  Angew Chem Int Ed Engl       Date:  2011-06-08       Impact factor: 15.336

6.  Thionoglycine as a multifunctional spectroscopic reporter of screw-sense preference in helical foldamers.

Authors:  Matteo De Poli; Jonathan Clayden
Journal:  Org Biomol Chem       Date:  2013-12-12       Impact factor: 3.876

Review 7.  Gly-X-Y tripeptide frequencies in collagen: a context for host-guest triple-helical peptides.

Authors:  J A Ramshaw; N K Shah; B Brodsky
Journal:  J Struct Biol       Date:  1998       Impact factor: 2.867

Review 8.  Collagen structure and stability.

Authors:  Matthew D Shoulders; Ronald T Raines
Journal:  Annu Rev Biochem       Date:  2009       Impact factor: 23.643

9.  Cis-trans proline isomerization effects on collagen triple-helix stability are limited.

Authors:  Nan Dai; Felicia A Etzkorn
Journal:  J Am Chem Soc       Date:  2009-09-30       Impact factor: 15.419

10.  Nature of amide carbonyl--carbonyl interactions in proteins.

Authors:  Amit Choudhary; Deepa Gandla; Grant R Krow; Ronald T Raines
Journal:  J Am Chem Soc       Date:  2009-06-03       Impact factor: 15.419
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  13 in total

Review 1.  Biosynthesis and Chemical Applications of Thioamides.

Authors:  Nilkamal Mahanta; D Miklos Szantai-Kis; E James Petersson; Douglas A Mitchell
Journal:  ACS Chem Biol       Date:  2019-01-30       Impact factor: 5.100

2.  Heterogeneous-Backbone Foldamer Mimics of Zinc Finger Tertiary Structure.

Authors:  Kelly L George; W Seth Horne
Journal:  J Am Chem Soc       Date:  2017-06-05       Impact factor: 15.419

3.  Thioamide Substitution Selectively Modulates Proteolysis and Receptor Activity of Therapeutic Peptide Hormones.

Authors:  Xing Chen; Elizabeth G Mietlicki-Baase; Taylor M Barrett; Lauren E McGrath; Kieran Koch-Laskowski; John J Ferrie; Matthew R Hayes; E James Petersson
Journal:  J Am Chem Soc       Date:  2017-11-13       Impact factor: 15.419

4.  Hydrogen Bond and Geometry Effects of Thioamide Backbone Modifications.

Authors:  Bryan J Lampkin; Brett VanVeller
Journal:  J Org Chem       Date:  2021-12-01       Impact factor: 4.354

5.  Structural impact of thioamide incorporation into a β-hairpin.

Authors:  Kristen E Fiore; Martijn J Patist; Sam Giannakoulias; Cheng-Hsin Huang; Hitesh Verma; Bhavesh Khatri; Richard P Cheng; Jayanta Chatterjee; E James Petersson
Journal:  RSC Chem Biol       Date:  2022-04-05

6.  Chemoselective modifications for the traceless ligation of thioamide-containing peptides and proteins.

Authors:  Yanxin J Wang; D Miklos Szantai-Kis; E James Petersson
Journal:  Org Biomol Chem       Date:  2016-06-06       Impact factor: 3.876

7.  A Single Stereodynamic Center Modulates the Rate of Self-Assembly in a Biomolecular System.

Authors:  Yitao Zhang; Roy M Malamakal; David M Chenoweth
Journal:  Angew Chem Int Ed Engl       Date:  2015-07-23       Impact factor: 15.336

8.  Dithioamide substitutions in proteins: effects on thermostability, peptide binding, and fluorescence quenching in calmodulin.

Authors:  Christopher R Walters; John J Ferrie; E James Petersson
Journal:  Chem Commun (Camb)       Date:  2018-02-13       Impact factor: 6.222

9.  Electronic interactions of i, i + 1 dithioamides: increased fluorescence quenching and evidence for n-to-π* interactions.

Authors:  Yun Huang; John J Ferrie; Xing Chen; Yitao Zhang; D Miklos Szantai-Kis; David M Chenoweth; E James Petersson
Journal:  Chem Commun (Camb)       Date:  2016-06-14       Impact factor: 6.222

10.  Increasing protein stability by engineering the n → π* interaction at the β-turn.

Authors:  Bhavesh Khatri; Puja Majumder; Jayashree Nagesh; Aravind Penmatsa; Jayanta Chatterjee
Journal:  Chem Sci       Date:  2020-07-30       Impact factor: 9.825
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