Literature DB >> 22332757

Advances in proline ligation.

Steven D Townsend1, Zhongping Tan, Suwei Dong, Shiying Shang, John A Brailsford, Samuel J Danishefsky.   

Abstract

Application of native chemical ligation logic to the case of an N-terminal proline is described. Two approaches were studied. One involved incorporation of a 3R-substituted thiyl-proline derivative. Improved results were obtained from a 3R-substituted selenol function, incorporated in the context of an oxidized dimer.
© 2012 American Chemical Society

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Year:  2012        PMID： 22332757      PMCID： PMC3306728          DOI： 10.1021/ja212182q

Source DB:  PubMed          Journal:  J Am Chem Soc        ISSN： 0002-7863            Impact factor:   15.419


  22 in total

1.  Preformed selenoesters enable rapid native chemical ligation at intractable sites.

Authors:  Thomas Durek; Paul F Alewood
Journal:  Angew Chem Int Ed Engl       Date:  2011-10-13       Impact factor: 15.336

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

Authors:  Samuel B Pollock; Stephen B H Kent
Journal:  Chem Commun (Camb)       Date:  2010-12-21       Impact factor: 6.222

3.  Free-radical-based, specific desulfurization of cysteine: a powerful advance in the synthesis of polypeptides and glycopolypeptides.

Authors:  Qian Wan; Samuel J Danishefsky
Journal:  Angew Chem Int Ed Engl       Date:  2007       Impact factor: 15.336

4.  Native chemical ligation at valine.

Authors:  Christian Haase; Heike Rohde; Oliver Seitz
Journal:  Angew Chem Int Ed Engl       Date:  2008       Impact factor: 15.336

5.  Native chemical ligation at valine: a contribution to peptide and glycopeptide synthesis.

Authors:  Jin Chen; Qian Wan; Yu Yuan; Jianglong Zhu; Samuel J Danishefsky
Journal:  Angew Chem Int Ed Engl       Date:  2008       Impact factor: 15.336

6.  Dual native chemical ligation at lysine.

Authors:  Renliang Yang; Kalyan Kumar Pasunooti; Fupeng Li; Xue-Wei Liu; Chuan-Fa Liu
Journal:  J Am Chem Soc       Date:  2009-09-30       Impact factor: 15.419

7.  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

8.  A program for ligation at threonine sites: application to the controlled total synthesis of glycopeptides.

Authors:  Jin Chen; Ping Wang; Jianglong Zhu; Qian Wan; Samuel J Danishefsky
Journal:  Tetrahedron       Date:  2010-03-27       Impact factor: 2.457

9.  Traceless ligation of cysteine peptides using selective deselenization.

Authors:  Norman Metanis; Ehud Keinan; Philip E Dawson
Journal:  Angew Chem Int Ed Engl       Date:  2010-09-17       Impact factor: 15.336

10.  Toward Homogeneous Erythropoietin: Application of Metal Free Dethiylation in the Chemical Synthesis of the Ala79-Arg166 Glycopeptide Domain.

Authors:  Suwei Dong; Shiying Shang; Zhongping Tan; Samuel J Danishefsky
Journal:  Isr J Chem       Date:  2011-11       Impact factor: 3.333
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  13 in total

1.  Metal-Assisted Folding of Prolinomycin Allows Facile Design of Functional Peptides.

Authors:  Azade S Hosseini; Wenjian Wang; Fredrik Haeffner; Jianmin Gao
Journal:  Chembiochem       Date:  2017-02-02       Impact factor: 3.164

2.  Expressed protein ligation at methionine: N-terminal attachment of homocysteine, ligation, and masking.

Authors:  Tomohiro Tanaka; Anne M Wagner; John B Warner; Yanxin J Wang; E James Petersson
Journal:  Angew Chem Int Ed Engl       Date:  2013-04-29       Impact factor: 15.336

Review 3.  Total synthesis of glycosylated proteins.

Authors:  Alberto Fernández-Tejada; John Brailsford; Qiang Zhang; Jae-Hung Shieh; Malcolm A S Moore; Samuel J Danishefsky
Journal:  Top Curr Chem       Date:  2015

Review 4.  Synthesis and semisynthesis of selenopeptides and selenoproteins.

Authors:  Jun Liu; Rujin Cheng; Sharon Rozovsky
Journal:  Curr Opin Chem Biol       Date:  2018-04-30       Impact factor: 8.822

5.  Proline editing: a general and practical approach to the synthesis of functionally and structurally diverse peptides. Analysis of steric versus stereoelectronic effects of 4-substituted prolines on conformation within peptides.

Authors:  Anil K Pandey; Devan Naduthambi; Krista M Thomas; Neal J Zondlo
Journal:  J Am Chem Soc       Date:  2013-03-11       Impact factor: 15.419

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.  Selective desulfurization significantly expands sequence variety of 3'-peptidyl-tRNA mimics obtained by native chemical ligation.

Authors:  Anna-Skrollan Geiermann; Ronald Micura
Journal:  Chembiochem       Date:  2012-07-11       Impact factor: 3.164

Review 8.  Chemical reactions directed Peptide self-assembly.

Authors:  Dnyaneshwar B Rasale; Apurba K Das
Journal:  Int J Mol Sci       Date:  2015-05-13       Impact factor: 5.923

9.  Realizing serine/threonine ligation: scope and limitations and mechanistic implication thereof.

Authors:  Clarence T T Wong; Tianlu Li; Hiu Yung Lam; Yinfeng Zhang; Xuechen Li
Journal:  Front Chem       Date:  2014-05-20       Impact factor: 5.221

10.  Traceless β-mercaptan-assisted activation of valinyl benzimidazolinones in peptide ligations.

Authors:  Yinglu Wang; Lin Han; Ning Yuan; Hanxuan Wang; Hongxing Li; Jinrong Liu; Huan Chen; Qiang Zhang; Suwei Dong
Journal:  Chem Sci       Date:  2018-01-05       Impact factor: 9.825
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