skip to main content
DOE PAGES title logo U.S. Department of Energy
Office of Scientific and Technical Information

This content will become publicly available on October 10, 2020

Title: Tailoring chemoenzymatic oxidation via in situ peracids

Abstract

Epoxidation chemistry often suffers from the challenging handling of peracids and thus requires in situ preparation.

Authors:
ORCiD logo [1];  [1]; ORCiD logo [1]; ORCiD logo [2]; ORCiD logo [1]
  1. Department of Chemistry and Biochemistry, UC San Diego, La Jolla, USA
  2. Department of Chemistry and Biochemistry, UC San Diego, La Jolla, USA, UMR IATE
Publication Date:
Sponsoring Org.:
USDOE Office of Energy Efficiency and Renewable Energy (EERE)
OSTI Identifier:
1571831
Grant/Contract Number:  
EE0008246
Resource Type:
Publisher's Accepted Manuscript
Journal Name:
Organic and Biomolecular Chemistry
Additional Journal Information:
Journal Name: Organic and Biomolecular Chemistry Journal Volume: 17 Journal Issue: 43; Journal ID: ISSN 1477-0520
Publisher:
Royal Society of Chemistry (RSC)
Country of Publication:
United Kingdom
Language:
English

Citation Formats

Re, Rebecca N., Proessdorf, Johanna C., La Clair, James J., Subileau, Maeva, and Burkart, Michael D. Tailoring chemoenzymatic oxidation via in situ peracids. United Kingdom: N. p., 2019. Web. doi:10.1039/C9OB01814J.
Re, Rebecca N., Proessdorf, Johanna C., La Clair, James J., Subileau, Maeva, & Burkart, Michael D. Tailoring chemoenzymatic oxidation via in situ peracids. United Kingdom. doi:10.1039/C9OB01814J.
Re, Rebecca N., Proessdorf, Johanna C., La Clair, James J., Subileau, Maeva, and Burkart, Michael D. Wed . "Tailoring chemoenzymatic oxidation via in situ peracids". United Kingdom. doi:10.1039/C9OB01814J.
@article{osti_1571831,
title = {Tailoring chemoenzymatic oxidation via in situ peracids},
author = {Re, Rebecca N. and Proessdorf, Johanna C. and La Clair, James J. and Subileau, Maeva and Burkart, Michael D.},
abstractNote = {Epoxidation chemistry often suffers from the challenging handling of peracids and thus requires in situ preparation.},
doi = {10.1039/C9OB01814J},
journal = {Organic and Biomolecular Chemistry},
number = 43,
volume = 17,
place = {United Kingdom},
year = {2019},
month = {11}
}

Journal Article:
Free Publicly Available Full Text
This content will become publicly available on October 10, 2020
Publisher's Version of Record

Save / Share:

Works referenced in this record:

An “Aprotic” Tamao Oxidation/ Syn -Selective Tautomerization Reaction for the Efficient Synthesis of the C(1)–C(9) Fragment of Fludelone
journal, September 2012

  • Harrison, Tyler J.; Rabbat, Philippe M. A.; Leighton, James L.
  • Organic Letters, Vol. 14, Issue 18
  • DOI: 10.1021/ol302221s

Substrate specificity of the lipase fromCandida parapsilosis
journal, August 1995

  • Briand, Delphine; Dubreucq, Eric; Grimaud, Jean
  • Lipids, Vol. 30, Issue 8
  • DOI: 10.1007/BF02537802

Synthesis of sulfoxides by oxidation of thioethers
journal, January 1986


Homologous yeast lipases/acyltransferases exhibit remarkable cold-active properties
journal, April 2014

  • Neang, Pisey M.; Subileau, Maeva; Perrier, Véronique
  • Applied Microbiology and Biotechnology, Vol. 98, Issue 21
  • DOI: 10.1007/s00253-014-5776-6

Triterpenoid total synthesis. Synthesis and absolute configuration of mispyric acidTriterpenoid total synthesis. Part 8. For part 7 see ref. 1
journal, January 2004

  • Imamura, Yusuke; Takikawa, Hirosato; Sasaki, Mitsuru
  • Organic & Biomolecular Chemistry, Vol. 2, Issue 15
  • DOI: 10.1039/b406820c

Oxydation ungesättigter Verbindungen mittels organischer Superoxyde
journal, November 1909


Enzymatic fatty esters synthesis in aqueous medium with lipase from Candida parapsilosis (Ashford) Langeron and Talice
journal, August 1994

  • Briand, D.; Dubreucq, E.; Galzy, P.
  • Biotechnology Letters, Vol. 16, Issue 8
  • DOI: 10.1007/BF00133959

6,7-epoxy-linalool and related oxygenated terpenoids from Carica papaya fruit
journal, May 1986


Antimycobacterial Activity of ( E )-Phytol and Derivatives: A Preliminary Structure-Activity Study
journal, February 1998

  • Rajab, Mohamed; Cantrell, Charles; Franzblau, Scott
  • Planta Medica, Vol. 64, Issue 01
  • DOI: 10.1055/s-2006-957354

Advances in Homogeneous and Heterogeneous Catalytic Asymmetric Epoxidation
journal, May 2005

  • Xia, Q. -H.; Ge, H. -Q.; Ye, C. -P.
  • Chemical Reviews, Vol. 105, Issue 5
  • DOI: 10.1021/cr0406458

Oxidative Desulfurization I: Peroxyformic Acid Oxidation of Benzothiophene and Dibenzothiophene
journal, May 2010

  • De Filippis, Paolo; Scarsella, Marco; Verdone, Nicola
  • Industrial & Engineering Chemistry Research, Vol. 49, Issue 10
  • DOI: 10.1021/ie9017622

Molecular Recognition in (+)-α-Pinene Oxidation by Cytochrome P450 cam
journal, January 2003

  • Bell, Stephen G.; Chen, Xuehui; Sowden, Rebecca J.
  • Journal of the American Chemical Society, Vol. 125, Issue 3
  • DOI: 10.1021/ja028460a

Mechanistic insights into the malonoyl peroxide syn-dihydroxylation of alkenes
journal, January 2014

  • Rawling, Michael J.; Rowley, Julian H.; Campbell, Matthew
  • Chem. Sci., Vol. 5, Issue 5
  • DOI: 10.1039/C3SC53256A

Development of Globo-H Cancer Vaccine
journal, February 2015

  • Danishefsky, Samuel J.; Shue, Youe-Kong; Chang, Michael N.
  • Accounts of Chemical Research, Vol. 48, Issue 3
  • DOI: 10.1021/ar5004187

Stereochemistry of 14-hydroxy-β-caryophyllene and related compounds
journal, March 1995


A synthetic entry to pladienolide B and FD-895
journal, September 2007

  • Mandel, Alexander L.; Jones, Brian D.; La Clair, James J.
  • Bioorganic & Medicinal Chemistry Letters, Vol. 17, Issue 18
  • DOI: 10.1016/j.bmcl.2007.06.094

Terpenes and isoprenoids: a wealth of compounds for global use
journal, November 2018


Biocatalytic Oxidation Reactions: A Chemist's Perspective
journal, July 2018

  • Dong, JiaJia; Fernández-Fueyo, Elena; Hollmann, Frank
  • Angewandte Chemie International Edition, Vol. 57, Issue 30
  • DOI: 10.1002/anie.201800343

The 3D model of the lipase/acyltransferase from Candida parapsilosis, a tool for the elucidation of structural determinants in CAL-A lipase superfamily
journal, October 2015

  • Subileau, Maeva; Jan, Anne-Hélène; Nozac'h, Hervé
  • Biochimica et Biophysica Acta (BBA) - Proteins and Proteomics, Vol. 1854, Issue 10
  • DOI: 10.1016/j.bbapap.2015.06.012

The use of lipases as biocatalysts for the epoxidation of fatty acids and phenolic compounds
journal, January 2014

  • Aouf, Chahinez; Durand, Erwann; Lecomte, Jérôme
  • Green Chem., Vol. 16, Issue 4
  • DOI: 10.1039/C3GC42143K

Total Synthesis of the Ansamycin Antibiotic (+)-Thiazinotrienomycin E
journal, June 2000

  • Smith, Amos B.; Wan, Zehong
  • The Journal of Organic Chemistry, Vol. 65, Issue 12
  • DOI: 10.1021/jo991958j

Structure of a Novel Enzyme That Catalyzes Acyl Transfer to Alcohols in Aqueous Conditions
journal, August 2007

  • Mathews, Irimpan; Soltis, Michael; Saldajeno, Mae
  • Biochemistry, Vol. 46, Issue 31
  • DOI: 10.1021/bi7002444

Enzymatic synthesis of perlauric acid using Novozym 435
journal, March 2002


Synthesis and antiproliferative activity of new tonantzitlolone-derived diterpene derivatives
journal, January 2016

  • Busch, Torsten; Dräger, Gerald; Kunst, Eike
  • Organic & Biomolecular Chemistry, Vol. 14, Issue 38
  • DOI: 10.1039/C6OB01697A

Atypical regioselective biohydrolysis on steroidal oxiranes by Aspergillus niger whole cells: Some stereochemical features
journal, July 2007


A strategy for the solid-phase synthesis of oligosaccharides
journal, May 1993


Enantioselective epoxidation of olefins with chiral metalloporphyrin catalysts
journal, January 2005

  • Rose, Eric; Andrioletti, Bruno; Zrig, Samia
  • Chemical Society Reviews, Vol. 34, Issue 7
  • DOI: 10.1039/b405679p

Synthetic and biological catalysts in chemical synthesis: how to assess practical utility
journal, October 1994


Asymmetric Organocatalytic Epoxidations: Reactions, Scope, Mechanisms, and Applications
journal, June 2014

  • Davis, Rebecca L.; Stiller, Julian; Naicker, Tricia
  • Angewandte Chemie International Edition, Vol. 53, Issue 29
  • DOI: 10.1002/anie.201400241

Lipases from Candida a ntarctica : Unique Biocatalysts from a Unique Origin
journal, July 2002

  • Kirk, Ole; Christensen, Morten Würtz
  • Organic Process Research & Development, Vol. 6, Issue 4
  • DOI: 10.1021/op0200165

Technological Aspects of Chemoenzymatic Epoxidation of Fatty Acids, Fatty Acid Esters and Vegetable Oils: A Review
journal, December 2015


Lipase-catalysed Baeyer–Villiger reactions
journal, January 1995

  • Lemoult, Stephanie C.; Richardson, Paul F.; Roberts, Stanley M.
  • J. Chem. Soc., Perkin Trans. 1, Issue 2
  • DOI: 10.1039/P19950000089

An Efficient Stereoselective Dihydroxylation of Glycals using a Bimetallic System, RuCl 3 /CeCl 3 /NaIO 4
journal, March 2006

  • Tiwari, Pallavi; Misra, Anup Kumar
  • The Journal of Organic Chemistry, Vol. 71, Issue 7
  • DOI: 10.1021/jo0526385

Peculiar features of four enzymes of the CaLA superfamily in aqueous media: Differences in substrate specificities and abilities to catalyze alcoholysis
journal, October 2013


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
journal, February 2016

  • Jan, Anne-Hélène; Subileau, Maeva; Deyrieux, Charlotte
  • Biochimica et Biophysica Acta (BBA) - Proteins and Proteomics, Vol. 1864, Issue 2
  • DOI: 10.1016/j.bbapap.2015.11.006

Olefin epoxidation with metal-based nanocatalysts
journal, July 2018


Critical Influence of 5-Hydroxymethylfurfural Aging and Decomposition on the Utility of Biomass Conversion in Organic Synthesis
journal, June 2016

  • Galkin, Konstantin I.; Krivodaeva, Elena A.; Romashov, Leonid V.
  • Angewandte Chemie International Edition, Vol. 55, Issue 29
  • DOI: 10.1002/anie.201602883

Biosynthesis of ethers: Unusual or common natural events?
journal, January 2010

  • Domínguez de María, Pablo; van Gemert, Robert W.; Straathof, Adrie J. J.
  • Natural Product Reports, Vol. 27, Issue 3
  • DOI: 10.1039/b809416k

NAD(P)H-Independent Asymmetric CC Bond Reduction Catalyzed by Ene Reductases by Using Artificial Co-substrates as the Hydrogen Donor
journal, December 2013

  • Winkler, Christoph K.; Clay, Dorina; Entner, Marcello
  • Chemistry - A European Journal, Vol. 20, Issue 5
  • DOI: 10.1002/chem.201303897

Chemo-enzymatic epoxidation of unsaturated carboxylic acids
journal, December 1995


Epoxidation and Reduction of DHEA, 1,4,6-Androstatrien-3-one and 4,6-Androstadien-3β,17β-diol
journal, March 2005


Stability of immobilized Candida antarctica lipase B during chemo-enzymatic epoxidation of fatty acids
journal, February 2007


Highly Enantioselective Bioinspired Epoxidation of Electron-Deficient Olefins with H 2 O 2 on Aminopyridine Mn Catalysts
journal, April 2014

  • Ottenbacher, Roman V.; Samsonenko, Denis G.; Talsi, Evgenii P.
  • ACS Catalysis, Vol. 4, Issue 5
  • DOI: 10.1021/cs500333c

Chemoenzymatic epoxidation of alkenes based on peracid formation by a Rhizomucor miehei lipase-catalyzed perhydrolysis reaction
journal, February 2014

  • Méndez-Sánchez, Daniel; Ríos-Lombardía, Nicolás; Gotor, Vicente
  • Tetrahedron, Vol. 70, Issue 6
  • DOI: 10.1016/j.tet.2013.12.084

Stereoselective Tandem Epoxidation-Alcoholysis/Hydrolysis of Glycals with Molybdenum Catalysts
journal, December 2010

  • Marín, Irene; Matheu, M. Isabel; Díaz, Yolanda
  • Advanced Synthesis & Catalysis, Vol. 352, Issue 18
  • DOI: 10.1002/adsc.201000614

Lipase-mediated formation of peroxycarboxylic acids used in catalytic epoxidation of alkenes
journal, January 1990

  • Björkling, Fredrik; Godtfredsen, Sven Erik; Kirk, Ole
  • J. Chem. Soc., Chem. Commun., Issue 19
  • DOI: 10.1039/C39900001301

Enzymatic acylation of the polar dipeptide, carnosine: Reaction performances in organic and aqueous media
journal, April 2011


Lipase catalyzed synthesis of peroxycarboxylic acids and lipase mediated oxidations.
journal, January 1992


Copper-Catalyzed γ-Selective and Stereospecific Allylic Cross-Coupling with Secondary Alkylboranes
journal, May 2015

  • Yasuda, Yuto; Nagao, Kazunori; Shido, Yoshinori
  • Chemistry - A European Journal, Vol. 21, Issue 27
  • DOI: 10.1002/chem.201501055

Convergent Total Syntheses of Oligosaccharides by One-Pot Sequential Stereoselective Glycosylations
journal, September 2003

  • Hashihayata, Takashi; Ikegai, Kazuhiro; Takeuchi, Kazuya
  • Bulletin of the Chemical Society of Japan, Vol. 76, Issue 9
  • DOI: 10.1246/bcsj.76.1829

Chemoenzymatic epoxidation of citronellol catalyzed by lipases
journal, March 2012


Novel methods for the preparation of partially acetylated carbohydrates
journal, July 1990


Direct Epoxidation in Candida antarctica Lipase B Studied by Experiment and Theory
journal, October 2008

  • Svedendahl, Maria; Carlqvist, Peter; Branneby, Cecilia
  • ChemBioChem, Vol. 9, Issue 15
  • DOI: 10.1002/cbic.200800318

Oxygenation of Monoenoic Fatty Acids by CYP175A1, an Orphan Cytochrome P450 from Thermus thermophilus HB27
journal, September 2012

  • Goyal, Sandeep; Banerjee, Shibdas; Mazumdar, Shyamalava
  • Biochemistry, Vol. 51, Issue 40
  • DOI: 10.1021/bi300514j

A novel and efficient catalytic epoxidation of olefins and monoterpenes with microencapsulated Lewis base adducts of methyltrioxorhenium
journal, January 2005


Characterization and Reshaping of a Large and Hydrophobic Nucleophile Pocket in Lipases/Acyltransferases
journal, August 2018

  • Jan Deniau, Anne-Hélène; Subileau, Maeva; Dubreucq, Eric
  • ChemBioChem, Vol. 19, Issue 17
  • DOI: 10.1002/cbic.201800279

Synthesis and Potent Antimalarial Activity of Kalihinol B
journal, April 2015

  • Daub, Mary Elisabeth; Prudhomme, Jacques; Le Roch, Karine
  • Journal of the American Chemical Society, Vol. 137, Issue 15
  • DOI: 10.1021/jacs.5b01152

Isomerization of α-pinene oxide over cerium and tin catalysts: Selective synthesis of trans-carveol and trans-sobrerol
journal, July 2011

  • Costa, Vinícius V.; da Silva Rocha, Kelly A.; de Sousa, Líniker F.
  • Journal of Molecular Catalysis A: Chemical, Vol. 345, Issue 1-2
  • DOI: 10.1016/j.molcata.2011.05.020

Metalloporphyrins: Bioinspired Oxidation Catalysts
journal, September 2018

  • Pereira, Mariette M.; Dias, Lucas D.; Calvete, Mário J. F.
  • ACS Catalysis, Vol. 8, Issue 11
  • DOI: 10.1021/acscatal.8b01871

Recent advances in the field of selective epoxidation of vegetable oils and their derivatives: a review and perspective
journal, January 2017

  • Danov, S. M.; Kazantsev, O. A.; Esipovich, A. L.
  • Catalysis Science & Technology, Vol. 7, Issue 17
  • DOI: 10.1039/C7CY00988G

Functional group selectivity in reactions of epoxides with tungsten hexachloride
journal, November 2007


Organocatalytic Asymmetric Epoxidation and Aziridination of Olefins and Their Synthetic Applications
journal, May 2014

  • Zhu, Yingguang; Wang, Qian; Cornwall, Richard G.
  • Chemical Reviews, Vol. 114, Issue 16
  • DOI: 10.1021/cr500064w

Recent developments on the epoxidation of alkenes using hydrogen peroxide as an oxidant
journal, December 2002

  • Grigoropoulou, G.; Clark, J. H.; Elings, J. A.
  • Green Chemistry, Vol. 5, Issue 1
  • DOI: 10.1039/b208925b

Emerging sustainable technology for epoxidation directed toward plant oil-based plasticizers
journal, October 2012


Hydrolase-catalysed synthesis of peroxycarboxylic acids: Biocatalytic promiscuity for practical applications
journal, November 2006

  • Carboni-Oerlemans, Chiara; Domínguez de María, Pablo; Tuin, Bernard
  • Journal of Biotechnology, Vol. 126, Issue 2
  • DOI: 10.1016/j.jbiotec.2006.04.008

What makes a lipase a valuable acyltransferase in water abundant medium?
journal, January 2017

  • Subileau, M.; Jan, A. H.; Drone, J.
  • Catalysis Science & Technology, Vol. 7, Issue 12
  • DOI: 10.1039/C6CY01805J

Synthetic Applications of Chiral Unsaturated Epoxy Alcohols Prepared by Sharpless Asymmetric Epoxidation
journal, February 2010


Lipase B from Candida antarctica immobilized on octadecyl Sepabeads: A very stable biocatalyst in the presence of hydrogen peroxide
journal, April 2011


Bridging the bridge—Stabilization of CalB against H2O2 and its application in epoxidation reactions
journal, November 2016


Development of a lipase-mediated epoxidation process for monoterpenes in choline chloride-based deep eutectic solvents
journal, January 2017

  • Ranganathan, Sumanth; Zeitlhofer, Sandra; Sieber, Volker
  • Green Chemistry, Vol. 19, Issue 11
  • DOI: 10.1039/C7GC01127J

meta-Chloroperbenzoic acid (mCPBA): a versatile reagent in organic synthesis
journal, January 2014

  • Hussain, Hidayat; Al-Harrasi, Ahmed; Green, Ivan R.
  • RSC Adv., Vol. 4, Issue 25
  • DOI: 10.1039/C3RA45702H

Highly Efficient Selective Oxygenation of Sulfides to Sulfoxides by Oxalic Acid Dihydrate in the Presence of H 2 O 2
journal, January 2012

  • Mokhtary, Masoud; Qandalee, Mohammad; Niaki, Masoumeh Rastegar
  • E-Journal of Chemistry, Vol. 9, Issue 2
  • DOI: 10.1155/2012/412798

Enzyme Catalyzed Degradation and Formation of Peroxycarboxylic Acids
journal, January 1994


Efficient conversion of (1R,5R)-(+)-.alpha.-pinene to (1S,5R)-(-)-nopinone
journal, April 1986

  • Lavallee, Pierre; Bouthillier, Gilles
  • The Journal of Organic Chemistry, Vol. 51, Issue 8
  • DOI: 10.1021/jo00358a041

Total Syntheses of Tumor-Related Antigens N3:  Probing the Feasibility Limits of the Glycal Assembly Method
journal, January 2001

  • Kim, Hyunjin M.; Kim, In Jong; Danishefsky, Samuel J.
  • Journal of the American Chemical Society, Vol. 123, Issue 1
  • DOI: 10.1021/ja0022730

Epoxidation of C-branched glycals: unexpected stereochemical results and their theoretical rationale
journal, January 2003


Fatty hydroxamic acid biosynthesis in aqueous medium in the presence of the lipase-acyltransferase from Candida parapsilosis
journal, February 1997


Synthesis of the fragrance terpene epoxides and selective monocyclization promoted by camphor and oxone®: Fragrance terpene epoxides and selective monocyclisation
journal, April 2016

  • Gaikwad, Ravindra D.; Kabiraj, Shilpi S.; Bhat, Sujata V.
  • Flavour and Fragrance Journal, Vol. 31, Issue 5
  • DOI: 10.1002/ffj.3322