Literature DB >> 29135064

Internal Peptide Late-Stage Diversification: Peptide-Isosteric Triazoles for Primary and Secondary C(sp3 )-H Activation.

Michaela Bauer1, Wei Wang1, Mélanie M Lorion1, Chuan Dong1, Lutz Ackermann1.   

Abstract

Secondary C(sp3 )-H arylations were accomplished by palladium catalysis with triazoles as peptide bond isosteres. The unique power of this approach is highlighted by the possibility of achieving secondary C(sp3 )-H functionalizations on terminal peptides as well as the unprecedented positional-selective C(sp3 )-H functionalization of internal peptide positions, setting the stage for modular peptide late-stage diversification.
© 2018 Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim.

Entities:  

Keywords:  amino acids; arylation; palladium; peptides; triazoles

Year:  2017        PMID： 29135064     DOI： 10.1002/anie.201710136

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


  15 in total

Review 1.  Transition-Metal-Catalyzed, Coordination-Assisted Functionalization of Nonactivated C(sp3)-H Bonds.

Authors:  Bin Liu; Andrew M Romine; Camille Z Rubel; Keary M Engle; Bing-Feng Shi
Journal:  Chem Rev       Date:  2021-10-29       Impact factor: 60.622

2.  Protecting group free radical C-H trifluoromethylation of peptides.

Authors:  Naoko Ichiishi; John P Caldwell; Melissa Lin; Wendy Zhong; Xiaohong Zhu; Eric Streckfuss; Hai-Young Kim; Craig A Parish; Shane W Krska
Journal:  Chem Sci       Date:  2018-04-10       Impact factor: 9.825

3.  Peptide-guided functionalization and macrocyclization of bioactive peptidosulfonamides by Pd(II)-catalyzed late-stage C-H activation.

Authors:  Jian Tang; Hongfei Chen; Yadong He; Wangjian Sheng; Qingqing Bai; Huan Wang
Journal:  Nat Commun       Date:  2018-08-23       Impact factor: 14.919

4.  Macrocyclization of peptidoarylacetamides with self-assembly properties through late-stage palladium-catalyzed C(sp2)▬H olefination.

Authors:  Jiantao Tan; Jie Wu; Shu Liu; Hequan Yao; Huan Wang
Journal:  Sci Adv       Date:  2019-03-08       Impact factor: 14.136

5.  Labeling and Natural Post-Translational Modification of Peptides and Proteins via Chemoselective Pd-Catalyzed Prenylation of Cysteine.

Authors:  Thomas Schlatzer; Julia Kriegesmann; Hilmar Schröder; Melanie Trobe; Christian Lembacher-Fadum; Simone Santner; Alexander V Kravchuk; Christian F W Becker; Rolf Breinbauer
Journal:  J Am Chem Soc       Date:  2019-09-09       Impact factor: 15.419

6.  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

7.  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

Review 8.  1,2,3-Triazoles as Biomimetics in Peptide Science.

Authors:  Naima Agouram; El Mestafa El Hadrami; Abdeslem Bentama
Journal:  Molecules       Date:  2021-05-14       Impact factor: 4.411

9.  Site-selective aqueous C-H acylation of tyrosine-containing oligopeptides with aldehydes.

Authors:  Marcos San Segundo; Arkaitz Correa
Journal:  Chem Sci       Date:  2020-10-06       Impact factor: 9.825

10.  An Organometallic Strategy for Cysteine Borylation.

Authors:  Mary A Waddington; Xin Zheng; Julia M Stauber; Elamar Hakim Moully; Hayden R Montgomery; Liban M A Saleh; Petr Král; Alexander M Spokoyny
Journal:  J Am Chem Soc       Date:  2021-06-01       Impact factor: 16.383
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