Literature DB >> 26037620

Late-Stage Peptide Diversification by Bioorthogonal Catalytic C-H Arylation at 23 °C in H2 O.

Yingjun Zhu1, Michaela Bauer1, Lutz Ackermann2.   

Abstract

The step-economical late-stage diversification of tryptophan-containing peptides was accomplished through chemo- and site-selective palladium-catalyzed C-H arylation under exceedingly mild reaction conditions. Thus, the C-H functionalization occurred efficiently at 23 °C with a catalyst loading as low as 0.5 mol %, and/or in H2 O.
© 2015 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim.

Entities:  

Keywords:  CH activation; H2O; chemoselectivity; late-stage derivatization; peptides

Mesh：

Substances：

Year:  2015        PMID： 26037620     DOI： 10.1002/chem.201501831

Source DB:  PubMed          Journal:  Chemistry        ISSN： 0947-6539            Impact factor:   5.236


  12 in total

1.  Palladium(II)-Catalyzed Site-Selective C(sp3 )-H Alkynylation of Oligopeptides: A Linchpin Approach for Oligopeptide-Drug Conjugation.

Authors:  Tao Liu; Jennifer X Qiao; Michael A Poss; Jin-Quan Yu
Journal:  Angew Chem Int Ed Engl       Date:  2017-08-07       Impact factor: 15.336

2.  S-Protected Cysteine Sulfoxide-Enabled Tryptophan-Selective Modification with Application to Peptide Lipidation.

Authors:  Daishiro Kobayashi; Eisuke Kuraoka; Junya Hayashi; Takuma Yasuda; Yutaka Kohmura; Masaya Denda; Norio Harada; Nobuya Inagaki; Akira Otaka
Journal:  ACS Med Chem Lett       Date:  2022-06-14       Impact factor: 4.632

Review 3.  Hypervalent Iodine-Mediated Late-Stage Peptide and Protein Functionalization.

Authors:  Emmanuelle M D Allouche; Elija Grinhagena; Jerome Waser
Journal:  Angew Chem Int Ed Engl       Date:  2021-12-08       Impact factor: 16.823

4.  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

Review 5.  Modern Synthetic Avenues for the Preparation of Functional Fluorophores.

Authors:  Fabio de Moliner; Nicola Kielland; Rodolfo Lavilla; Marc Vendrell
Journal:  Angew Chem Int Ed Engl       Date:  2017-02-17       Impact factor: 15.336

6.  Scalable thioarylation of unprotected peptides and biomolecules under Ni/photoredox catalysis.

Authors:  Brandon A Vara; Xingpin Li; Simon Berritt; Christopher R Walters; E James Petersson; Gary A Molander
Journal:  Chem Sci       Date:  2017-11-13       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.  Peptide late-stage C(sp3)-H arylation by native asparagine assistance without exogenous directing groups.

Authors:  Yiyi Weng; Xingxing Ding; João C A Oliveira; Xiaobin Xu; Nikolaos Kaplaneris; Meijie Zhu; Hantao Chen; Zhuo Chen; Lutz Ackermann
Journal:  Chem Sci       Date:  2020-08-12       Impact factor: 9.825

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.  Combining Sanford Arylations on Benzodiazepines with the Nuisance Effect.

Authors:  Raysa Khan; Sarote Boonseng; Paul D Kemmitt; Robert Felix; Simon J Coles; Graham J Tizzard; Gareth Williams; Olivia Simmonds; Jessica-Lily Harvey; John Atack; Hazel Cox; John Spencer
Journal:  Adv Synth Catal       Date:  2017-08-02       Impact factor: 5.837
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