Literature DB >> 21173985

An investigation into the origin of the dramatically reduced reactivity of peptide-prolyl-thioesters in native chemical ligation.

Samuel B Pollock1, Stephen B H Kent.   

Abstract

The low reactivity of peptide-prolyl-thioesters in native chemical ligation is not due to steric effects at the β-carbon, but rather to the presence of a carbonyl moiety on the nitrogen atom of the proline.

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Year:  2010        PMID： 21173985     DOI： 10.1039/c0cc04120c

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


  20 in total

1.  Traceless semisynthesis of a set of histone 3 species bearing specific lysine methylation marks.

Authors:  Zhonglei Chen; Adrian T Grzybowski; Alexander J Ruthenburg
Journal:  Chembiochem       Date:  2014-08-22       Impact factor: 3.164

2.  n→π* Interactions Are Competitive with Hydrogen Bonds.

Authors:  Robert W Newberry; Samuel J Orke; Ronald T Raines
Journal:  Org Lett       Date:  2016-07-13       Impact factor: 6.005

3.  Intimate interactions with carbonyl groups: dipole-dipole or n→π*?

Authors:  Kimberli J Kamer; Amit Choudhary; Ronald T Raines
Journal:  J Org Chem       Date:  2012-12-10       Impact factor: 4.354

4.  Advances in proline ligation.

Authors:  Steven D Townsend; Zhongping Tan; Suwei Dong; Shiying Shang; John A Brailsford; Samuel J Danishefsky
Journal:  J Am Chem Soc       Date:  2012-02-15       Impact factor: 15.419

5.  An advance in proline ligation.

Authors:  Shiying Shang; Zhongping Tan; Suwei Dong; Samuel J Danishefsky
Journal:  J Am Chem Soc       Date:  2011-06-23       Impact factor: 15.419

6.  Native Serine Peptide Assembly: Scope and Utility.

Authors:  Michael C Pirrung; Ryan S Schreihans
Journal:  European J Org Chem       Date:  2016-11-15

7.  A key n→π* Interaction in N-acyl homoserine lactones.

Authors:  Robert W Newberry; Ronald T Raines
Journal:  ACS Chem Biol       Date:  2014-02-26       Impact factor: 5.100

8.  Degradation of the acyl side chain of the steroid compound cholate in Pseudomonas sp. strain Chol1 proceeds via an aldehyde intermediate.

Authors:  Johannes Holert; Žarko Kulić; Onur Yücel; Vemparthan Suvekbala; Marc J-F Suter; Heiko M Möller; Bodo Philipp
Journal:  J Bacteriol       Date:  2012-11-30       Impact factor: 3.490

9.  n→π* interactions in poly(lactic acid) suggest a role in protein folding.

Authors:  Robert W Newberry; Ronald T Raines
Journal:  Chem Commun (Camb)       Date:  2013-09-11       Impact factor: 6.222

10.  An n→π* interaction reduces the electrophilicity of the acceptor carbonyl group.

Authors:  Amit Choudhary; Charles G Fry; Kimberli J Kamer; Ronald T Raines
Journal:  Chem Commun (Camb)       Date:  2013-09-25       Impact factor: 6.222
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