Literature DB >> 19191273

Efficient solid-phase synthesis of sulfotyrosine peptides using a sulfate protecting-group strategy.

Ahmed M Ali1, Scott D Taylor.   

Abstract

Double protection: Efficient Fmoc-based solid-phase synthesis (SPPS) of sulfotyrosine (sY) peptides is achieved by incorporating the sY residue(s) as a dichlorovinyl-protected (DCV) sulfodiester(s) and using 2-methylpiperidine for Fmoc removal. After removal of the other protecting groups, the DCV group could be cleaved by mild hydrogenolysis giving the sY peptides in good yield.

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Year:  2009        PMID： 19191273     DOI： 10.1002/anie.200805642

Source DB:  PubMed          Journal:  Angew Chem Int Ed Engl        ISSN： 1433-7851            Impact factor:   15.336


  8 in total

1.  Chemical Sulfation of Small Molecules - Advances and Challenges.

Authors:  Rami A Al-Horani; Umesh R Desai
Journal:  Tetrahedron       Date:  2010-04-17       Impact factor: 2.457

2.  Synthesis of Sulfotyrosine-Containing Peptides by Incorporating Fluorosulfated Tyrosine Using an Fmoc-Based Solid-Phase Strategy.

Authors:  Wentao Chen; Jiajia Dong; Suhua Li; Yu Liu; Yujia Wang; Leonard Yoon; Peng Wu; K Barry Sharpless; Jeffery W Kelly
Journal:  Angew Chem Int Ed Engl       Date:  2015-12-22       Impact factor: 15.336

3.  Template-constrained cyclic sulfopeptide HIV-1 entry inhibitors.

Authors:  Jonathan G Rudick; Meg M Laakso; Ashley C Schloss; William F DeGrado
Journal:  Org Biomol Chem       Date:  2013-11-07       Impact factor: 3.876

4.  Synthesis of O-Sulfated Human Syndecan-1-like Glyco-polypeptides by Incorporating Peptide Ligation and O-Sulfated Glycopeptide Cassette Strategies.

Authors:  Tianlu Li; Weizhun Yang; Sherif Ramadan; Xuefei Huang
Journal:  Org Lett       Date:  2020-08-06       Impact factor: 6.005

Review 5.  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

6.  Chemical synthesis of human syndecan-4 glycopeptide bearing O-, N-sulfation and multiple aspartic acids for probing impacts of the glycan chain and the core peptide on biological functions.

Authors:  Weizhun Yang; Yigitcan Eken; Jicheng Zhang; Logan Emerson Cole; Sherif Ramadan; Yongmei Xu; Zeren Zhang; Jian Liu; Angela K Wilson; Xuefei Huang
Journal:  Chem Sci       Date:  2020-05-11       Impact factor: 9.825

7.  Site-selective solid-phase synthesis of a CCR5 sulfopeptide library to interrogate HIV binding and entry.

Authors:  Xuyu Liu; Lara R Malins; Michael Roche; Jasminka Sterjovski; Renee Duncan; Mary L Garcia; Nadine C Barnes; David A Anderson; Martin J Stone; Paul R Gorry; Richard J Payne
Journal:  ACS Chem Biol       Date:  2014-07-24       Impact factor: 5.100

Review 8.  Chemical synthesis, backbone cyclization and oxidative folding of cystine-knot peptides: promising scaffolds for applications in drug design.

Authors:  Michael Reinwarth; Daichi Nasu; Harald Kolmar; Olga Avrutina
Journal:  Molecules       Date:  2012-10-24       Impact factor: 4.411
  8 in total

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