Literature DB >> 17177366

Remote desymmetrization at near-nanometer group separation catalyzed by a miniaturized enzyme mimic.

Chad A Lewis1, Anna Chiu, Michele Kubryk, Jaume Balsells, David Pollard, Craig K Esser, Jerry Murry, Robert A Reamer, Karl B Hansen, Scott J Miller.   

Abstract

The chirality of biological receptors often requires syntheses of therapeutic compounds in single enantiomer form. The field of asymmetric catalysis addresses enantioselective synthesis with chiral catalysts. Chemical differentiation of sites within molecules that are separated in space by long distances presents special challenges to chiral catalysts. As the distance between enantiotopic sites increases within a substrate, so too may the requirements for size and complexity for the catalyst. The extreme of catalyst complexity could be defined by macromolecular enzymes and their amazing capacity to effect stereospecific reactions over long distances between reactive sites and enzyme-substrate contacts. We report here a synthetic, miniaturized enzyme mimic that catalyzes a desymmetrization reaction over a very long distance.

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Year:  2006        PMID: 17177366     DOI: 10.1021/ja067840j

Source DB:  PubMed          Journal:  J Am Chem Soc        ISSN: 0002-7863            Impact factor:   15.419


  21 in total

1.  A General, Simple Catalyst for Enantiospecific Cross Couplings of Benzylic Ammonium Triflates and Boronic Acids: No Phosphine Ligand Required.

Authors:  Danielle M Shacklady-McAtee; Kelsey M Roberts; Corey H Basch; Ye-Geun Song; Mary P Watson
Journal:  Tetrahedron       Date:  2014-07-08       Impact factor: 2.457

2.  Linear free-energy relationship analysis of a catalytic desymmetrization reaction of a diarylmethane-bis(phenol).

Authors:  Jeffrey L Gustafson; Matthew S Sigman; Scott J Miller
Journal:  Org Lett       Date:  2010-06-18       Impact factor: 6.005

3.  Enantioselective Desymmetrization of Methylenedianilines via Enzyme-Catalyzed Remote Halogenation.

Authors:  James T Payne; Paul H Butkovich; Yifan Gu; Kyle N Kunze; Hyun June Park; Duo-Sheng Wang; Jared C Lewis
Journal:  J Am Chem Soc       Date:  2018-01-08       Impact factor: 15.419

4.  Nickel-catalyzed cross-couplings of benzylic pivalates with arylboroxines: stereospecific formation of diarylalkanes and triarylmethanes.

Authors:  Qi Zhou; Harathi D Srinivas; Srimoyee Dasgupta; Mary P Watson
Journal:  J Am Chem Soc       Date:  2013-02-20       Impact factor: 15.419

5.  Enantioselective sulfonylation reactions mediated by a tetrapeptide catalyst.

Authors:  Kristin Williams Fiori; Angela L A Puchlopek; Scott J Miller
Journal:  Nat Chem       Date:  2009-11       Impact factor: 24.427

6.  Enantioselective Intermolecular C-O Bond Formation in the Desymmetrization of Diarylmethines Employing a Guanidinylated Peptide-Based Catalyst.

Authors:  Alex J Chinn; Byoungmoo Kim; Yongseok Kwon; Scott J Miller
Journal:  J Am Chem Soc       Date:  2017-11-27       Impact factor: 15.419

7.  An approach to the site-selective diversification of apoptolidin A with peptide-based catalysts.

Authors:  Chad A Lewis; Kate E Longcore; Scott J Miller; Paul A Wender
Journal:  J Nat Prod       Date:  2009-10       Impact factor: 4.050

Review 8.  Asymmetric Catalysis Mediated by Synthetic Peptides, Version 2.0: Expansion of Scope and Mechanisms.

Authors:  Anthony J Metrano; Alex J Chinn; Christopher R Shugrue; Elizabeth A Stone; Byoungmoo Kim; Scott J Miller
Journal:  Chem Rev       Date:  2020-09-24       Impact factor: 60.622

9.  Asymmetric catalysis at a distance: catalytic, site-selective phosphorylation of teicoplanin.

Authors:  Sunkyu Han; Scott J Miller
Journal:  J Am Chem Soc       Date:  2013-08-07       Impact factor: 15.419

10.  Site-selective catalysis of phenyl thionoformate transfer as a tool for regioselective deoxygenation of polyols.

Authors:  María Sanchez-Roselló; Angela L A Puchlopek; Adam J Morgan; Scott J Miller
Journal:  J Org Chem       Date:  2008-01-30       Impact factor: 4.354

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