Literature DB >> 31650153

Tailoring chemoenzymatic oxidation via in situ peracids.

Rebecca N Re1, Johanna C Proessdorf, James J La Clair, Maeva Subileau, Michael D Burkart.   

Abstract

Epoxidation chemistry often suffers from the challenging handling of peracids and thus requires in situ preparation. Here, we describe a two-phase enzymatic system that allows the effective generation of peracids and directly translate their activity to the epoxidation of olefins. We demonstrate the approach by application to lipid and olefin epoxidation as well as sulfide oxidation. These methods offer useful applications to synthetic modifications and scalable green processes.

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Year:  2019        PMID: 31650153      PMCID: PMC7751277          DOI: 10.1039/c9ob01814j

Source DB:  PubMed          Journal:  Org Biomol Chem        ISSN: 1477-0520            Impact factor:   3.876


  42 in total

Review 1.  Enantioselective epoxidation of olefins with chiral metalloporphyrin catalysts.

Authors:  Eric Rose; Bruno Andrioletti; Samia Zrig; Mélanie Quelquejeu-Ethève
Journal:  Chem Soc Rev       Date:  2005-04-18       Impact factor: 54.564

Review 2.  Synthetic and biological catalysts in chemical synthesis: how to assess practical utility.

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Journal:  Chem Biol       Date:  1994-10

3.  Characterization and Reshaping of a Large and Hydrophobic Nucleophile Pocket in Lipases/Acyltransferases.

Authors:  Anne-Hélène Jan Deniau; Maeva Subileau; Eric Dubreucq
Journal:  Chembiochem       Date:  2018-08-08       Impact factor: 3.164

4.  How the Same Core Catalytic Machinery Catalyzes 17 Different Reactions: the Serine-Histidine-Aspartate Catalytic Triad of α/β-Hydrolase Fold Enzymes.

Authors:  Alissa Rauwerdink; Romas J Kazlauskas
Journal:  ACS Catal       Date:  2015-09-09       Impact factor: 13.084

5.  A strategy for the solid-phase synthesis of oligosaccharides.

Authors:  S J Danishefsky; K F McClure; J T Randolph; R B Ruggeri
Journal:  Science       Date:  1993-05-28       Impact factor: 47.728

6.  Epoxidation of C-branched glycals: unexpected stereochemical results and their theoretical rationale.

Authors:  Christiane Ernst; Manuel Piacenza; Stefan Grimme; Werner Klaffke
Journal:  Carbohydr Res       Date:  2003-01-31       Impact factor: 2.104

7.  An efficient stereoselective dihydroxylation of glycals using a bimetallic system, RuCl3/CeCl3/NaIO4.

Authors:  Pallavi Tiwari; Anup Kumar Misra
Journal:  J Org Chem       Date:  2006-03-31       Impact factor: 4.354

8.  Elucidation of a key position for acyltransfer activity in Candida parapsilosis lipase/acyltransferase (CpLIP2) and in Pseudozyma antarctica lipase A (CAL-A) by rational design.

Authors:  Anne-Hélène Jan; Maeva Subileau; Charlotte Deyrieux; Véronique Perrier; Éric Dubreucq
Journal:  Biochim Biophys Acta       Date:  2015-11-18

Review 9.  Synthetic applications of chiral unsaturated epoxy alcohols prepared by sharpless asymmetric epoxidation.

Authors:  Antoni Riera; María Moreno
Journal:  Molecules       Date:  2010-02-23       Impact factor: 4.411

10.  Epoxidation and reduction of DHEA, 1,4,6-androstatrien-3-one and 4,6-androstadien-3beta,17beta-diol.

Authors:  Eunsook Ma; Eunjeong Kim
Journal:  Molecules       Date:  2005-05-25       Impact factor: 4.411

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  1 in total

1.  Sequence-Based Prediction of Promiscuous Acyltransferase Activity in Hydrolases.

Authors:  Henrik Müller; Ann-Kristin Becker; Gottfried J Palm; Leona Berndt; Christoffel P S Badenhorst; Simon P Godehard; Lukas Reisky; Michael Lammers; Uwe T Bornscheuer
Journal:  Angew Chem Int Ed Engl       Date:  2020-05-11       Impact factor: 15.336

  1 in total

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