Literature DB >> 23865986

Synthesis of C-2 arylated tryptophan amino acids and related compounds through palladium-catalyzed C-H activation.

Sara Preciado1, Lorena Mendive-Tapia, Fernando Albericio, Rodolfo Lavilla.   

Abstract

Tryptophan (Trp) and tryptophan derivatives are C2-arylated. A C-H activation process allows the preparation of both protected and unprotected arylated-Trp amino acids, directly from the amino acid precursor and aryl iodides. The obtained compounds are suitable for standard solid-phase peptide synthesis.

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Year:  2013        PMID： 23865986     DOI： 10.1021/jo400961x

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


  12 in total

1.  Preparation of a Trp-BODIPY fluorogenic amino acid to label peptides for enhanced live-cell fluorescence imaging.

Authors:  Lorena Mendive-Tapia; Ramon Subiros-Funosas; Can Zhao; Fernando Albericio; Nick D Read; Rodolfo Lavilla; Marc Vendrell
Journal:  Nat Protoc       Date:  2017-07-13       Impact factor: 13.491

2.  New peptide architectures through C-H activation stapling between tryptophan-phenylalanine/tyrosine residues.

Authors:  Lorena Mendive-Tapia; Sara Preciado; Jesús García; Rosario Ramón; Nicola Kielland; Fernando Albericio; Rodolfo Lavilla
Journal:  Nat Commun       Date:  2015-05-21       Impact factor: 14.919

3.  Room-Temperature Direct β-Arylation of Thiophenes and Benzo[b]thiophenes and Kinetic Evidence for a Heck-type Pathway.

Authors:  Chiara Colletto; Saidul Islam; Francisco Juliá-Hernández; Igor Larrosa
Journal:  J Am Chem Soc       Date:  2016-01-28       Impact factor: 15.419

4.  Ru-catalysed C-H arylation of indoles and pyrroles with boronic acids: scope and mechanistic studies.

Authors:  Carina Sollert; Karthik Devaraj; Andreas Orthaber; Paul J Gates; Lukasz T Pilarski
Journal:  Chemistry       Date:  2015-02-17       Impact factor: 5.236

5.  Mild and Regioselective Pd(OAc)2-Catalyzed C-H Arylation of Tryptophans by [ArN2]X, Promoted by Tosic Acid.

Authors:  Alan J Reay; L Anders Hammarback; Joshua T W Bray; Thomas Sheridan; David Turnbull; Adrian C Whitwood; Ian J S Fairlamb
Journal:  ACS Catal       Date:  2017-07-10       Impact factor: 13.084

6.  The α-tertiary amine motif drives remarkable selectivity for Pd-catalyzed carbonylation of β-methylene C-H bonds.

Authors:  Kirsten F Hogg; Aaron Trowbridge; Andrea Alvarez-Pérez; Matthew J Gaunt
Journal:  Chem Sci       Date:  2017-10-09       Impact factor: 9.825

7.  Late-stage C(sp2)-H and C(sp3)-H glycosylation of C-aryl/alkyl glycopeptides: mechanistic insights and fluorescence labeling.

Authors:  Jun Wu; Nikolaos Kaplaneris; Shaofei Ni; Felix Kaltenhäuser; Lutz Ackermann
Journal:  Chem Sci       Date:  2020-03-24       Impact factor: 9.825

8.  Synthesis of 2-substituted tryptophans via a C3- to C2-alkyl migration.

Authors:  Michele Mari; Simone Lucarini; Francesca Bartoccini; Giovanni Piersanti; Gilberto Spadoni
Journal:  Beilstein J Org Chem       Date:  2014-08-26       Impact factor: 2.883

9.  Gold-catalyzed direct alkynylation of tryptophan in peptides using TIPS-EBX.

Authors:  Gergely L Tolnai; Jonathan P Brand; Jerome Waser
Journal:  Beilstein J Org Chem       Date:  2016-04-19       Impact factor: 2.883

10.  Spacer-free BODIPY fluorogens in antimicrobial peptides for direct imaging of fungal infection in human tissue.

Authors:  Lorena Mendive-Tapia; Can Zhao; Ahsan R Akram; Sara Preciado; Fernando Albericio; Martin Lee; Alan Serrels; Nicola Kielland; Nick D Read; Rodolfo Lavilla; Marc Vendrell
Journal:  Nat Commun       Date:  2016-03-09       Impact factor: 14.919
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