Literature DB >> 21916403

Mixed-phase synthesis of glycopeptides using a N-peptidyl-2,4-dinitrobenzenesulfonamide-thioacid ligation strategy.

Partha Karmakar1, Rommel S Talan, Steven J Sucheck.   

Abstract

A strategy for the solid phase peptide synthesis (SPPS) and coupling of N-peptidyl and N-glycopeptidyl 2,4-dinitrobenzenesulfonamides (dNBS) with C-terminal peptidyl thioacids has been developed. The resulting N-dDNBS peptides were coupled to generate longer peptides. Ligation reactions were complete within 15 to 20 min.
© 2011 American Chemical Society

Entities:  

Mesh:

Substances:

Year:  2011        PMID: 21916403      PMCID: PMC3188410          DOI: 10.1021/ol202163e

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


  13 in total

Review 1.  Chemical synthesis of proteins.

Authors:  Bradley L Nilsson; Matthew B Soellner; Ronald T Raines
Journal:  Annu Rev Biophys Biomol Struct       Date:  2005

2.  Development of efficient methods for accomplishing cysteine-free peptide and glycopeptide coupling.

Authors:  Gong Chen; Qian Wan; Zhongping Tan; Cindy Kan; Zihao Hua; Krishnakumar Ranganathan; Samuel J Danishefsky
Journal:  Angew Chem Int Ed Engl       Date:  2007       Impact factor: 15.336

3.  The epithelial tumor antigen MUC1 is expressed in hematological malignancies and is recognized by MUC1-specific cytotoxic T-lymphocytes.

Authors:  P Brossart; A Schneider; P Dill; T Schammann; F Grünebach; S Wirths; L Kanz; H J Bühring; W Brugger
Journal:  Cancer Res       Date:  2001-09-15       Impact factor: 12.701

4.  Molecular cloning and expression of human tumor-associated polymorphic epithelial mucin.

Authors:  S J Gendler; C A Lancaster; J Taylor-Papadimitriou; T Duhig; N Peat; J Burchell; L Pemberton; E N Lalani; D Wilson
Journal:  J Biol Chem       Date:  1990-09-05       Impact factor: 5.157

5.  Synthesis of a single-molecule L-rhamnose-containing three-component vaccine and evaluation of antigenicity in the presence of anti-L-rhamnose antibodies.

Authors:  Sourav Sarkar; Steven A Lombardo; Danielle N Herner; Rommel S Talan; Katherine A Wall; Steven J Sucheck
Journal:  J Am Chem Soc       Date:  2010-11-16       Impact factor: 15.419

6.  Solid-phase synthesis and characterization of N-methyl-rich peptides.

Authors:  M Teixidó; F Albericio; E Giralt
Journal:  J Pept Res       Date:  2005-02

Review 7.  MUC-1 epithelial tumor mucin-based immunity and cancer vaccines.

Authors:  O J Finn; K R Jerome; R A Henderson; G Pecher; N Domenech; J Magarian-Blander; S M Barratt-Boyes
Journal:  Immunol Rev       Date:  1995-06       Impact factor: 12.988

8.  One-pot syntheses of dissymmetric diamides based on the chemistry of cyclic monothioanhydrides. Scope and limitations and application to the synthesis of glycodipeptides.

Authors:  David Crich; Kaname Sasaki; Md Yeajur Rahaman; Albert A Bowers
Journal:  J Org Chem       Date:  2009-05-15       Impact factor: 4.354

9.  Facile synthesis of N-glycosyl amides using a N-glycosyl-2,4-dinitrobenzenesulfonamide and thioacids.

Authors:  Rommel S Talan; Aditya K Sanki; Steven J Sucheck
Journal:  Carbohydr Res       Date:  2009-07-12       Impact factor: 2.104

10.  Triblock peptide and peptide thioester synthesis with reactivity-differentiated sulfonamides and peptidyl thioacids.

Authors:  David Crich; Indrajeet Sharma
Journal:  Angew Chem Int Ed Engl       Date:  2009       Impact factor: 15.336

View more
  3 in total

1.  Fully Synthetic Granulocyte Colony-Stimulating Factor Enabled by Isonitrile-Mediated Coupling of Large, Side-Chain-Unprotected Peptides.

Authors:  Andrew G Roberts; Eric V Johnston; Jae-Hung Shieh; Joseph P Sondey; Ronald C Hendrickson; Malcolm A S Moore; Samuel J Danishefsky
Journal:  J Am Chem Soc       Date:  2015-10-01       Impact factor: 15.419

2.  Synthesis of β-Glycosyl Amides from N-Glycosyl Dinitrobenzenesulfonamides.

Authors:  Vishwanath Gaitonde; Steven J Sucheck
Journal:  J Carbohydr Chem       Date:  2012-07-02       Impact factor: 1.667

3.  Combining triazole ligation and enzymatic glycosylation on solid phase simplifies the synthesis of very long glycoprotein analogues.

Authors:  Mathieu Galibert; Véronique Piller; Friedrich Piller; Vincent Aucagne; Agnès F Delmas
Journal:  Chem Sci       Date:  2015-04-14       Impact factor: 9.825

  3 in total

北京卡尤迪生物科技股份有限公司 © 2022-2023.