Literature DB >> 26498123

Functionalization of protected tyrosine via Sonogashira reaction: synthesis of 3-(1,2,3-triazolyl)-tyrosine.

Stanley N S Vasconcelos1, Anwar Shamim2, Bakhat Ali1, Isadora M de Oliveira3, Hélio A Stefani4.   

Abstract

1,2,3-Triazol tyrosines were synthesized from tyrosine alkynes that were in turn prepared via Sonogashira cross-coupling reaction. The tyrosine alkynes were subjected to click-chemistry reaction conditions leading to the corresponding 3-(1,2,3-triazolyl)-tyrosines in yields ranging from moderate to good.

Entities:  

Keywords:  Alkyne; Click chemistry; Peptide bond; Triazole; Tyrosine

Mesh：

Substances：

Year:  2015        PMID： 26498123     DOI： 10.1007/s11030-015-9642-y

Source DB:  PubMed          Journal:  Mol Divers        ISSN： 1381-1991            Impact factor:   2.943


  19 in total

1.  Chemical modification of M13 bacteriophage and its application in cancer cell imaging.

Authors:  Kai Li; Yi Chen; Siqi Li; Huong Giang Nguyen; Zhongwei Niu; Shaojin You; Charlene M Mello; Xiaobing Lu; Qian Wang
Journal:  Bioconjug Chem       Date:  2010-07-21       Impact factor: 4.774

2.  Site-specific protein cross-linking by peroxidase-catalyzed activation of a tyrosine-containing peptide tag.

Authors:  Kosuke Minamihata; Masahiro Goto; Noriho Kamiya
Journal:  Bioconjug Chem       Date:  2010-12-13       Impact factor: 4.774

3.  Proton-coupled electron transfer from tyrosine: a strong rate dependence on intramolecular proton transfer distance.

Authors:  Ming-Tian Zhang; Tania Irebo; Olof Johansson; Leif Hammarström
Journal:  J Am Chem Soc       Date:  2011-08-09       Impact factor: 15.419

4.  Dual-surface modification of the tobacco mosaic virus.

Authors:  Tara L Schlick; Zhebo Ding; Ernest W Kovacs; Matthew B Francis
Journal:  J Am Chem Soc       Date:  2005-03-23       Impact factor: 15.419

5.  A three-component Mannich-type reaction for selective tyrosine bioconjugation.

Authors:  Neel S Joshi; Leanna R Whitaker; Matthew B Francis
Journal:  J Am Chem Soc       Date:  2004-12-15       Impact factor: 15.419

6.  Direct peptide bioconjugation/PEGylation at tyrosine with linear and branched polymeric diazonium salts.

Authors:  Mathew W Jones; Giuseppe Mantovani; Claudia A Blindauer; Sinead M Ryan; Xuexuan Wang; David J Brayden; David M Haddleton
Journal:  J Am Chem Soc       Date:  2012-04-21       Impact factor: 15.419

7.  Facile and stabile linkages through tyrosine: bioconjugation strategies with the tyrosine-click reaction.

Authors:  Hitoshi Ban; Masanobu Nagano; Julia Gavrilyuk; Wataru Hakamata; Tsubasa Inokuma; Carlos F Barbas
Journal:  Bioconjug Chem       Date:  2013-03-27       Impact factor: 4.774

8.  Characterization of a three-component coupling reaction on proteins by isotopic labeling and nuclear magnetic resonance spectroscopy.

Authors:  Jesse M McFarland; Neel S Joshi; Matthew B Francis
Journal:  J Am Chem Soc       Date:  2008-05-23       Impact factor: 15.419

9.  Tyrosine bioconjugation through aqueous ene-type reactions: a click-like reaction for tyrosine.

Authors:  Hitoshi Ban; Julia Gavrilyuk; Carlos F Barbas
Journal:  J Am Chem Soc       Date:  2010-02-10       Impact factor: 15.419

10.  Interior surface modification of bacteriophage MS2.

Authors:  Jacob M Hooker; Ernest W Kovacs; Matthew B Francis
Journal:  J Am Chem Soc       Date:  2004-03-31       Impact factor: 15.419
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  1 in total

1.  Efficient one-pot synthesis of new 1-amino substituted pyrrolo[1,2-a]quinoline-4-carboxylate esters via copper-free Sonogashira coupling reactions.

Authors:  Ali Keivanloo; Shaghayegh Sadat Kazemi; Hossein Nasr-Isfahani; Abdolhamid Bamoniri
Journal:  Mol Divers       Date:  2016-09-06       Impact factor: 2.943
  1 in total

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