Literature DB >> 28944064

De novo synthesis of alkyne substituted tryptophans as chemical probes for protein profiling studies.

R N Nair1,2, J J Rosnow1, T A Murphree1, M E Bowden1, S R Lindemann3, A T Wright1.   

Abstract

De novo synthesis of alkynalted tryptophan moieties as chemical probes for protein profilling studies, via an unexpected synthesis of Michael acceptor 12 is reported. Friedel Craft's alkylation of 12 and alkyne substituted indoles gave alkynalated tryptophan moieties, which perform as chemical probe by incorporating into actively translating Escherichia coli cells, whereby the alkyne moiety enables multimodal analyses through click chemistry mediated attachment of reporting groups.

Entities:  

Year:  2016        PMID: 28944064      PMCID: PMC5607013          DOI: 10.1039/C6QO00819D

Source DB:  PubMed          Journal:  Org Chem Front        ISSN: 2052-4110            Impact factor:   5.281


  23 in total

1.  Single bifunctional ruthenium catalyst for one-pot cyclization and hydration giving functionalized indoles and benzofurans.

Authors:  Reji N Nair; Paul J Lee; Arnold L Rheingold; Douglas B Grotjahn
Journal:  Chemistry       Date:  2010-07-19       Impact factor: 5.236

2.  Live Cell Discovery of Microbial Vitamin Transport and Enzyme-Cofactor Interactions.

Authors:  Lindsey N Anderson; Phillip K Koech; Andrew E Plymale; Elizabeth V Landorf; Allan Konopka; Frank R Collart; Mary S Lipton; Margaret F Romine; Aaron T Wright
Journal:  ACS Chem Biol       Date:  2015-12-22       Impact factor: 5.100

Review 3.  Design and engineering of metalloproteins containing unnatural amino acids or non-native metal-containing cofactors.

Authors:  Yi Lu
Journal:  Curr Opin Chem Biol       Date:  2005-04       Impact factor: 8.822

4.  A facile system for encoding unnatural amino acids in mammalian cells.

Authors:  Peng R Chen; Dan Groff; Jiantao Guo; Weijia Ou; Susan Cellitti; Bernhard H Geierstanger; Peter G Schultz
Journal:  Angew Chem Int Ed Engl       Date:  2009       Impact factor: 15.336

5.  Organelle-specific activity-based protein profiling in living cells.

Authors:  Susan D Wiedner; Lindsey N Anderson; Natalie C Sadler; William B Chrisler; Vamsi K Kodali; Richard D Smith; Aaron T Wright
Journal:  Angew Chem Int Ed Engl       Date:  2014-02-06       Impact factor: 15.336

6.  Labeling, detection and identification of newly synthesized proteomes with bioorthogonal non-canonical amino-acid tagging.

Authors:  Daniela C Dieterich; Jennifer J Lee; A James Link; Johannes Graumann; David A Tirrell; Erin M Schuman
Journal:  Nat Protoc       Date:  2007       Impact factor: 13.491

7.  Use of a boroxazolidone complex of 3-iodo-L-tyrosine for palladium-catalyzed cross-coupling.

Authors:  William H Walker; Steven E Rokita
Journal:  J Org Chem       Date:  2003-02-21       Impact factor: 4.354

8.  Developing new chemical tools for DNA methyltransferase 1 (DNMT 1): a small-molecule activity-based probe and novel tetrazole-containing inhibitors.

Authors:  Biwei Zhu; Jingyan Ge; Shao Q Yao
Journal:  Bioorg Med Chem       Date:  2015-03-10       Impact factor: 3.641

9.  Catalytic asymmetric synthesis of protected tryptophan regioisomers.

Authors:  Paul R Carlier; Polo C-H Lam; Dawn M Wong
Journal:  J Org Chem       Date:  2002-08-23       Impact factor: 4.354

10.  In situ visualization of newly synthesized proteins in environmental microbes using amino acid tagging and click chemistry.

Authors:  Roland Hatzenpichler; Silvan Scheller; Patricia L Tavormina; Brett M Babin; David A Tirrell; Victoria J Orphan
Journal:  Environ Microbiol       Date:  2014-04-02       Impact factor: 5.491

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