Chloroperoxidase and hydrogen peroxide: An efficient system for enzymatic enantioselective sulfoxidations.

Colonna, Stefano; Gaggero, Nicoletta; Casella, Luigi; Carrea, Giacomo; Pasta, Piero

doi:10.1016/s0957-4166(00)82316-2

Cited by 170 publications

(65 citation statements)

References 31 publications

Supporting

Mentioning

Contrasting

Unclassified

Order By: Relevance

“…Furthermore, CPO has a unique ability to utilize halide (except fluoride) ions to halogenate a wide variety of organic acceptor molecules in the presence of hydrogen peroxide or other organic hydroperoxides (14 -16). Most importantly, CPO is adept in catalyzing the stereoselective epoxidation of alkenes (10,17,18), hydroxylation of alkynes (19,20), and oxidation of organic sulfides (21)(22)(23).…”

mentioning

confidence: 99%

Two-dimensional NMR Study of the Heme Active Site Structure of Chloroperoxidase

Wang

Tachikawa

et al. 2003

Journal of Biological Chemistry

View full text Add to dashboard Cite

show abstract

mentioning

confidence: 99%

Two-dimensional NMR Study of the Heme Active Site Structure of Chloroperoxidase

Wang

Tachikawa

et al. 2003

Journal of Biological Chemistry

View full text Add to dashboard Cite

show abstract

“…Colonna demonstrated that the optimum oxidant for use with CPO is hydrogen peroxide, obtaining sulfoxides in high yield and enantiopurity. 195 Significant achiral oxidation can occur in these oxidations which is not catalyzed by CPO; this can be avoided by the use of conditions proposed by Sheldon. 196,197 The first electroenzymatic asymmetric sulfide oxidation was reported using the CPO enzyme from Caldariomyces fumago.…”

mentioning

confidence: 99%

Synthesis of enantioenriched sulfoxides

O’Mahony¹,

Kelly²,

Lawrence³

et al. 2011

Arkivoc

View full text Add to dashboard Cite

This review discusses strategies for the asymmetric synthesis of sulfoxides, compounds with many applications in stereoselective synthesis and in some cases with pharmaceutical application. The review describes asymmetric oxidation, including metal catalyzed and nonmetal and biological oxidation processes, in addition to synthetic approaches via nucleophilic substitution of appropriately substituted precursors. Kinetic resolution in oxidation of sulfoxides to the analogous sulfones is also discussed; in certain instances, access to enantioenriched sulfoxides can be achieved via a combination of asymmetric sulfide oxidation and complementary kinetic resolution in sulfoxide oxidation.

show abstract

“…Especially peroxidases efficiently catalyze the enantioselective sulfoxidation of a variety of sulfides (4,11,23). Several whole-cell systems have also been successfully employed in biocatalytic sulfoxidation; among them, some bacterial strains hold great promise for the development of environmentally benign, efficient asymmetric sulfoxidation (16,19,22).…”

mentioning

confidence: 99%

Opposite Enantioselectivities of Two Phenotypically and Genotypically Similar Strains of Pseudomonas frederiksbergensis in Bacterial Whole-Cell Sulfoxidation

Adam

Heckel

Saha‐Möller³

et al. 2005

Appl Environ Microbiol

View full text Add to dashboard Cite

Soil samples were screened to select microorganisms with the capability to oxidize organic sulfides into the corresponding sulfoxides with differential enantioselectivities. Several bacterial strains that preferentially produced the S-configured sulfoxide enantiomer were isolated. Surprisingly, one bacterial strain, genotypically and phenotypically characterized as Pseudomonas frederiksbergensis, selectively gave the R enantiomer. The finding that two apparently identical organisms displayed opposite enantioselectivities is novel for nongenetically modified organisms.

show abstract

Chloroperoxidase and hydrogen peroxide: An efficient system for enzymatic enantioselective sulfoxidations.

Cited by 170 publications

References 31 publications

Two-dimensional NMR Study of the Heme Active Site Structure of Chloroperoxidase

Two-dimensional NMR Study of the Heme Active Site Structure of Chloroperoxidase

Synthesis of enantioenriched sulfoxides

Opposite Enantioselectivities of Two Phenotypically and Genotypically Similar Strains of Pseudomonas frederiksbergensis in Bacterial Whole-Cell Sulfoxidation

Contact Info

Product

Resources

About