Literature DB >> 11123884

Synthetic catalysis of amide isomerization.

C Cox1, T Lectka.   

Abstract

Rotation about the C-N bond in amides can be catalyzed by Bronsted and Lewis acids, as well as nucleophiles and bases. Catalysis of amide isomerization occurs in biological systems via "rotamase" enzymes; however, the mechanisms by which these proteins operate are not completely understood. We outline investigations that provide experimental support for mechanisms believed to be feasible for the catalysis of amide isomerization and present practical applications that have resulted from this work.

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Year:  2000        PMID： 11123884     DOI： 10.1021/ar990165g

Source DB:  PubMed          Journal:  Acc Chem Res        ISSN： 0001-4842            Impact factor:   22.384


  12 in total

1.  Structural characterization of N-protonated amides: regioselective N-activation of medium-bridged twisted lactams.

Authors:  Michal Szostak; Lei Yao; Victor W Day; Douglas R Powell; Jeffrey Aubé
Journal:  J Am Chem Soc       Date:  2010-07-07       Impact factor: 15.419

2.  Malleable conformation of the elastic PEVK segment of titin: non-co-operative interconversion of polyproline II helix, beta-turn and unordered structures.

Authors:  Kan Ma; Kuan Wang
Journal:  Biochem J       Date:  2003-09-15       Impact factor: 3.857

Review 3.  Chemistry of bridged lactams and related heterocycles.

Authors:  Michal Szostak; Jeffrey Aubé
Journal:  Chem Rev       Date:  2013-06-17       Impact factor: 60.622

4.  Friedel-Crafts acylation with amides.

Authors:  Erum K Raja; Daniel J DeSchepper; Sten O Nilsson Lill; Douglas A Klumpp
Journal:  J Org Chem       Date:  2012-06-21       Impact factor: 4.354

5.  An efficient computational model to predict protonation at the amide nitrogen and reactivity along the C-N rotational pathway.

Authors:  Roman Szostak; Jeffrey Aubé; Michal Szostak
Journal:  Chem Commun (Camb)       Date:  2015-04-14       Impact factor: 6.222

6.  Pyramidalization/twisting of the amide functional group via remote steric congestion triggered by metal coordination.

Authors:  Shinya Adachi; Naoya Kumagai; Masakatsu Shibasaki
Journal:  Chem Sci       Date:  2016-09-23       Impact factor: 9.825

7.  Palladium-catalyzed decarbonylative Suzuki-Miyaura cross-coupling of amides by carbon-nitrogen bond activation.

Authors:  Tongliang Zhou; Chong-Lei Ji; Xin Hong; Michal Szostak
Journal:  Chem Sci       Date:  2019-09-03       Impact factor: 9.825

8.  Highly chemoselective reduction of amides (primary, secondary, tertiary) to alcohols using SmI2/amine/H2O under mild conditions.

Authors:  Michal Szostak; Malcolm Spain; Andrew J Eberhart; David J Procter
Journal:  J Am Chem Soc       Date:  2014-01-31       Impact factor: 15.419

9.  Spontaneous transfer of chirality in an atropisomerically enriched two-axis system.

Authors:  Kimberly T Barrett; Anthony J Metrano; Paul R Rablen; Scott J Miller
Journal:  Nature       Date:  2014-04-20       Impact factor: 49.962

10.  Bispidine Platform as a Tool for Studying Amide Configuration Stability.

Authors:  Dmitry P Krut'ko; Alexey V Medved'ko; Konstantin A Lyssenko; Andrei V Churakov; Alexander I Dalinger; Mikhail A Kalinin; Alexey O Gudovannyy; Konstantin Y Ponomarev; Eugeny V Suslov; Sergey Z Vatsadze
Journal:  Molecules       Date:  2022-01-10       Impact factor: 4.411
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