Literature DB >> 19161341

N-->S acyl-transfer-mediated synthesis of peptide thioesters using anilide derivatives.

Shugo Tsuda1, Akira Shigenaga, Kiyomi Bando, Akira Otaka.   

Abstract

N-->S acyl-transfer-mediated synthesis of peptide thioesters utilizing an N-aminoacyl-N-sulfanylethylaminobenzoic acid derivative has been examined. The developed synthetic methodology for peptide thioesters is compatible with Fmoc solid-phase peptide synthesis (SPPS).

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Year:  2009        PMID： 19161341     DOI： 10.1021/ol8028093

Source DB:  PubMed          Journal:  Org Lett        ISSN： 1523-7052            Impact factor:   6.005


  12 in total

1.  Chemical synthesis of proteins using peptide hydrazides as thioester surrogates.

Authors:  Ji-Shen Zheng; Shan Tang; Yun-Kun Qi; Zhi-Peng Wang; Lei Liu
Journal:  Nat Protoc       Date:  2013-11-14       Impact factor: 13.491

2.  N-methylcysteine-mediated total chemical synthesis of ubiquitin thioester.

Authors:  Lesly A Erlich; K S Ajish Kumar; Mahmood Haj-Yahya; Philip E Dawson; Ashraf Brik
Journal:  Org Biomol Chem       Date:  2010-03-11       Impact factor: 3.876

3.  Alternative chemistries for the synthesis of thrombospondin-1 type 1 repeats.

Authors:  Theresa K Tiefenbrunn; Juan Blanco-Canosa; Philip E Dawson
Journal:  Biopolymers       Date:  2010       Impact factor: 2.505

Review 4.  Expanding the chemical toolbox for the synthesis of large and uniquely modified proteins.

Authors:  Somasekhar Bondalapati; Muhammad Jbara; Ashraf Brik
Journal:  Nat Chem       Date:  2016-04-22       Impact factor: 24.427

5.  Protein chemical synthesis by α-ketoacid-hydroxylamine ligation.

Authors:  Thibault J Harmand; Claudia E Murar; Jeffrey W Bode
Journal:  Nat Protoc       Date:  2016-05-26       Impact factor: 13.491

6.  Native N-glycopeptide thioester synthesis through N→S acyl transfer.

Authors:  Bhavesh Premdjee; Anna L Adams; Derek Macmillan
Journal:  Bioorg Med Chem Lett       Date:  2011-05-25       Impact factor: 2.823

7.  Shifting Native Chemical Ligation into Reverse through N→S Acyl Transfer.

Authors:  Derek Macmillan; Anna Adams; Bhavesh Premdjee
Journal:  Isr J Chem       Date:  2011-10-05       Impact factor: 3.333

8.  Development of a Chemical Methodology for the Preparation of Peptide Thioesters Applicable to Naturally Occurring Peptides Using a Sequential Quadruple Acyl Transfer System.

Authors:  Yusuke Tsuda; Akira Shigenaga; Kohei Tsuji; Masaya Denda; Kohei Sato; Keisuke Kitakaze; Takahiro Nakamura; Tsubasa Inokuma; Kohji Itoh; Akira Otaka
Journal:  ChemistryOpen       Date:  2015-04-28       Impact factor: 2.911

Review 9.  Advances in Fmoc solid-phase peptide synthesis.

Authors:  Raymond Behrendt; Peter White; John Offer
Journal:  J Pept Sci       Date:  2016-01       Impact factor: 1.905

10.  Accelerating chemoselective peptide bond formation using bis(2-selenylethyl)amido peptide selenoester surrogates.

Authors:  Laurent Raibaut; Marine Cargoët; Nathalie Ollivier; Yun Min Chang; Hervé Drobecq; Emmanuelle Boll; Rémi Desmet; Jean-Christophe M Monbaliu; Oleg Melnyk
Journal:  Chem Sci       Date:  2016-01-11       Impact factor: 9.825
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