Literature DB >> 27934446

Stereoselective Peptide Modifications via β-C(sp3)-H Arylations.

Biplab Mondal1,2, Brindaban Roy2, Uli Kazmaier1.   

Abstract

Palladium-catalyzed stereoselective β-arylations of phenylalanine, proline- and pipecolinic acid-containing peptides are a versatile tool for peptide modifications. The reactions proceed without epimerization of stereogenic centers in the peptide chain. If suitable functionalized aryl iodides are introduced, subsequent cross coupling reactions can be used for further modifications. The 8-amino quinoline (AQ) directing group can easily be removed, allowing the prolongation of the peptide chain at the C-terminus.

Entities:  

Year:  2016        PMID： 27934446     DOI： 10.1021/acs.joc.6b01963

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


  5 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

Review 2.  A comprehensive overview of directing groups applied in metal-catalysed C-H functionalisation chemistry.

Authors:  Carlo Sambiagio; David Schönbauer; Remi Blieck; Toan Dao-Huy; Gerit Pototschnig; Patricia Schaaf; Thomas Wiesinger; Muhammad Farooq Zia; Joanna Wencel-Delord; Tatiana Besset; Bert U W Maes; Michael Schnürch
Journal:  Chem Soc Rev       Date:  2018-08-28       Impact factor: 54.564

3.  Directed C(sp3)-H arylation of tryptophan: transformation of the directing group into an activated amide.

Authors:  Lennart Nicke; Philip Horx; Klaus Harms; Armin Geyer
Journal:  Chem Sci       Date:  2019-08-08       Impact factor: 9.825

4.  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

5.  Synthesis of 3-Substituted Pyrrolidines via Palladium-Catalyzed Hydroarylation.

Authors:  Joseph B Sweeney; Julien Doulcet; Bimod Thapa
Journal:  iScience       Date:  2018-11-01
  5 in total

北京卡尤迪生物科技股份有限公司 © 2022-2023.