Literature DB >> 26543444

A Synergistic Combinatorial and Chiroptical Study of Peptide Catalysts for Asymmetric Baeyer-Villiger Oxidation.

Michael W Giuliano1, Chung-Yon Lin2, David K Romney1, Scott J Miller1, Eric V Anslyn2.   

Abstract

We report an approach to the asymmetric Baeyer-Villiger oxidation utilizing bioinformatics-inspired combinatorial screening for catalyst discovery. Scaled-up validation of our on-bead efforts with a circular dichroism-based assay of alcohols derived from the products of solution-phase reactions established the absolute configuration of lactone products; this assay proved equivalent to HPLC in its ability to evaluate catalyst performance, but was far superior in its speed of analysis. Further solution-phase screening of a focused library suggested a mode of asymmetric induction that draws distinct parallels with the mechanism of Baeyer-Villiger monooxygenases.

Entities:  

Keywords:  Baeyer-Villiger oxidation; catalysis; circular dichroism; peptides

Year:  2015        PMID： 26543444      PMCID： PMC4629862          DOI： 10.1002/adsc.201500230

Source DB:  PubMed          Journal:  Adv Synth Catal        ISSN： 1615-4150            Impact factor:   5.837


  29 in total

1.  A Demonstration of the Primary Stereoelectronic Effect in the Baeyer-Villiger Oxidation of alpha-Fluorocyclohexanones The Natural Sciences and Engineering Research Council of Canada (NSERC) is gratefully acknowledged for support of this research in terms of research grants to C.C. and PGS scholarships to A.C.C. We would especially like to thank Professor Scott E. Denmark, Dr. Robert Syvret, and Dr. Claudio Sturino for helpful discussions.

Authors: 
Journal:  Angew Chem Int Ed Engl       Date:  2000-08-18       Impact factor: 15.336

2.  Aspartate-catalyzed asymmetric epoxidation reactions.

Authors:  Gorka Peris; Charles E Jakobsche; Scott J Miller
Journal:  J Am Chem Soc       Date:  2007-06-26       Impact factor: 15.419

3.  Well Plate Circular Dichroism Reader for the Rapid Determination of Enantiomeric Excess.

Authors:  P Metola; S M Nichols; B Kahr; E V Anslyn
Journal:  Chem Sci       Date:  2014-11-01       Impact factor: 9.825

4.  Novel CalphaNN structural motif for protein recognition of phosphate ions.

Authors:  Konstantin A Denessiouk; Mark S Johnson; Alexander I Denesyuk
Journal:  J Mol Biol       Date:  2005-01-21       Impact factor: 5.469

5.  A novel main-chain anion-binding site in proteins: the nest. A particular combination of phi,psi values in successive residues gives rise to anion-binding sites that occur commonly and are found often at functionally important regions.

Authors:  James D Watson; E James Milner-White
Journal:  J Mol Biol       Date:  2002-01-11       Impact factor: 5.469

6.  Zr[bis(salicylidene)ethylenediaminato]-mediated Baeyer-Villiger oxidation: stereospecific synthesis of abnormal and normal lactones.

Authors:  Akira Watanabe; Tatsuya Uchida; Ryo Irie; Tsutomu Katsuki
Journal:  Proc Natl Acad Sci U S A       Date:  2004-04-08       Impact factor: 11.205

7.  A nonenzymatic acid/peracid catalytic cycle for the Baeyer-Villiger oxidation.

Authors:  Gorka Peris; Scott J Miller
Journal:  Org Lett       Date:  2008-06-14       Impact factor: 6.005

8.  Mechanistic investigation of chiral phosphoric acid catalyzed asymmetric Baeyer-Villiger reaction of 3-substituted cyclobutanones with H2O2 as the oxidant.

Authors:  Senmiao Xu; Zheng Wang; Yuxue Li; Xumu Zhang; Haiming Wang; Kuiling Ding
Journal:  Chemistry       Date:  2010-03-08       Impact factor: 5.236

9.  Combinatorial evolution of site- and enantioselective catalysts for polyene epoxidation.

Authors:  Phillip A Lichtor; Scott J Miller
Journal:  Nat Chem       Date:  2012-10-14       Impact factor: 24.427

10.  Experimental lineage and functional analysis of a remotely directed peptide epoxidation catalyst.

Authors:  Phillip A Lichtor; Scott J Miller
Journal:  J Am Chem Soc       Date:  2014-04-01       Impact factor: 15.419
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  8 in total

1.  Cu(ii)/SPDO complex catalyzed asymmetric Baeyer-Villiger oxidation of 2-arylcyclobutanones and its application for the total synthesis of eupomatilones 5 and 6.

Authors:  Chang-Sheng Zhang; Ya-Ping Shao; Fu-Min Zhang; Xue Han; Xiao-Ming Zhang; Kun Zhang; Yong-Qiang Tu
Journal:  Chem Sci       Date:  2022-06-23       Impact factor: 9.969

Review 2.  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

3.  Application of a High-Throughput Enantiomeric Excess Optical Assay Involving a Dynamic Covalent Assembly: Parallel Asymmetric Allylation and Ee Sensing of Homoallylic Alcohols.

Authors:  H H Jo; X Gao; L You; E V Anslyn; M J Krische
Journal:  Chem Sci       Date:  2015-07-13       Impact factor: 9.825

4.  From Substituent Effects to Applications: Enhancing the Optical Response of a Four-Component Assembly for Reporting EE Values.

Authors:  Chung-Yon Lin; Michael W Giuliano; Bryan D Ellis; Scott J Miller; Eric V Anslyn
Journal:  Chem Sci       Date:  2016-03-07       Impact factor: 9.825

5.  Click chemistry enables quantitative chiroptical sensing of chiral compounds in protic media and complex mixtures.

Authors:  F Yushra Thanzeel; Kaluvu Balaraman; Christian Wolf
Journal:  Nat Commun       Date:  2018-12-14       Impact factor: 14.919

6.  Copper-catalyzed synthesis of 2-aminopyridylbenzoxazoles via domino reactions of intermolecular N-arylation and intramolecular O-arylation.

Authors:  Ju-You Lu
Journal:  RSC Adv       Date:  2019-05-01       Impact factor: 4.036

7.  Molecular Self-Assembly Strategy for Generating Catalytic Hybrid Polypeptides.

Authors:  Yoshiaki Maeda; Justin Fang; Yasuhiro Ikezoe; Douglas H Pike; Vikas Nanda; Hiroshi Matsui
Journal:  PLoS One       Date:  2016-04-26       Impact factor: 3.240

8.  Biocatalytic Conversion of Cyclic Ketones Bearing α-Quaternary Stereocenters into Lactones in an Enantioselective Radical Approach to Medium-Sized Carbocycles.

Authors:  Charlotte Morrill; Chantel Jensen; Xavier Just-Baringo; Gideon Grogan; Nicholas J Turner; David J Procter
Journal:  Angew Chem Int Ed Engl       Date:  2018-03-05       Impact factor: 15.336
  8 in total

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