Literature DB >> 21718046

Direct Fmoc-chemistry-based solid-phase synthesis of peptidyl thioesters.

Indrajeet Sharma1, David Crich.   

Abstract

Attachment of a growing peptide chain to a glycylaminomethyl resin via a thioglycinamide bond is compatible with Fmoc-chemistry solid-phase peptide synthesis. Subsequent S-alkylation of the thioamide gives a thioimide that, on treatment with aqueous trifluoroacetic acid, releases the peptide from the resin in the form of a C-terminal thioester.

Entities:  

Mesh：

Substances：

Year:  2011        PMID： 21718046      PMCID： PMC3184774          DOI： 10.1021/jo200497j

Source DB:  PubMed          Journal:  J Org Chem        ISSN： 0022-3263            Impact factor:   4.354


  41 in total

1.  Protein synthesis by native chemical ligation: expanded scope by using straightforward methodology.

Authors:  T M Hackeng; J H Griffin; P E Dawson
Journal:  Proc Natl Acad Sci U S A       Date:  1999-08-31       Impact factor: 11.205

2.  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

Review 3.  Evolving strategies for protein synthesis converge on native chemical ligation.

Authors:  Derek Macmillan
Journal:  Angew Chem Int Ed Engl       Date:  2006-11-27       Impact factor: 15.336

4.  Solid-phase synthesis of peptide thioesters with self-purification.

Authors:  Franziska Mende; Oliver Seitz
Journal:  Angew Chem Int Ed Engl       Date:  2007       Impact factor: 15.336

5.  Peptidyl N,N-bis(2-mercaptoethyl)-amides as thioester precursors for native chemical ligation.

Authors:  Wen Hou; Xiaohong Zhang; Fupeng Li; Chuan-Fa Liu
Journal:  Org Lett       Date:  2010-12-22       Impact factor: 6.005

6.  Probing substrate backbone function in prolyl oligopeptidase catalysis--large positional effects of peptide bond monothioxylation.

Authors:  M Schutkowski; M Jakob; G Landgraf; I Born; K Neubert; G Fischer
Journal:  Eur J Biochem       Date:  1997-04-15

7.  Native chemical ligation through in situ O to S acyl shift.

Authors:  Paolo Botti; Matteo Villain; Sonia Manganiello; Hubert Gaertner
Journal:  Org Lett       Date:  2004-12-23       Impact factor: 6.005

8.  Backbone Amide Linker (BAL) Strategy for N(alpha)()-9-Fluorenylmethoxycarbonyl (Fmoc) Solid-Phase Synthesis of Unprotected Peptide p-Nitroanilides and Thioesters(1).

Authors:  Jordi Alsina; T. Scott Yokum; Fernando Albericio; George Barany
Journal:  J Org Chem       Date:  1999-11-26       Impact factor: 4.354

9.  Efficient substitution reaction from cysteine to the serine residue of glycosylated polypeptide: repetitive peptide segment ligation strategy and the synthesis of glycosylated tetracontapeptide having acid labile sialyl-T(N) antigens.

Authors:  Ryo Okamoto; Shingo Souma; Yasuhiro Kajihara
Journal:  J Org Chem       Date:  2009-03-20       Impact factor: 4.354

10.  Chemical synthesis of a glycoprotein having an intact human complex-type sialyloligosaccharide under the Boc and Fmoc synthetic strategies.

Authors:  Naoki Yamamoto; Yasutaka Tanabe; Ryo Okamoto; Philip E Dawson; Yasuhiro Kajihara
Journal:  J Am Chem Soc       Date:  2007-12-18       Impact factor: 15.419
View more
  3 in total

1.  Solution-phase-peptide synthesis via the group-assisted purification (GAP) chemistry without using chromatography and recrystallization.

Authors:  Jianbin Wu; Guanghui An; Siqi Lin; Jianbo Xie; Wei Zhou; Hao Sun; Yi Pan; Guigen Li
Journal:  Chem Commun (Camb)       Date:  2014-02-07       Impact factor: 6.222

2.  Native chemical ligation of thioamide-containing peptides: development and application to the synthesis of labeled α-synuclein for misfolding studies.

Authors:  Solongo Batjargal; Yanxin J Wang; Jacob M Goldberg; Rebecca F Wissner; E James Petersson
Journal:  J Am Chem Soc       Date:  2012-04-02       Impact factor: 15.419

3.  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
  3 in total

北京卡尤迪生物科技股份有限公司 © 2022-2023.