Monoterpenes as novel substrates for oxidation and halo-hydroxylation with chloroperoxidase from Caldariomyces fumago

Applied Microbiology and Biotechnology
Bjoern-Arne KaupJens Schrader

Abstract

Chloroperoxidase (CPO) from Caldariomyces fumago was analysed for its ability to oxidize ten different monoterpenes with hydrogen peroxide as oxidant. In the absence of halide ions geraniol and, to a lesser extent, citronellol and nerol were converted into the corresponding aldehydes, whereas terpene hydrocarbons did not serve as substrates under these conditions. In the presence of chloride, bromide and iodide ions, every terpene tested was converted into one or more products. (1S)-(+)-3-carene was chosen as a model substrate for the CPO-catalysed conversion of terpenes in the presence of sodium halides. With chloride, bromide and iodide, the reaction products were the respective (1S,3R,4R,6R)-4-halo-3,7,7-trimethyl-bicyclo[4.1.0]-heptane-3-ols, as identified by 1H and 13C nuclear magnetic resonance. These product formations turned out to be strictly regio- and stereoselective and proceeded very rapidly and almost quantitatively. Initial specific activities of halohydrin formation increased from 4.22 U mg-1 with chloride to 12.22 U mg-1 with bromide and 37.11 U mg-1 with iodide as the respective halide ion. These results represent the first examples of the application of CPO as a highly efficient biocatalyst for monoterpene fu...Continue Reading

References

Jun 9, 1976·Journal of the American Chemical Society·J H DawsonLowell P. Hager
Aug 12, 1983·Biochemical and Biophysical Research Communications·J GeigertJ Wadsworth
Dec 5, 2000·Current Opinion in Biotechnology·F van Rantwijk, R A Sheldon
Apr 27, 2001·Toxicology Letters·M F Wilks
May 31, 2001·Archives of Microbiology·K H van Pée
May 31, 1996·The Journal of Organic Chemistry·Frederick J. Lakner, Lowell P. Hager
Dec 17, 2002·Current Opinion in Biotechnology·Vlada Urlacher, Rolf D Schmid
Mar 27, 2003·Journal of the American Chemical Society·Jayme N Carter-FranklinAlison Butler
May 10, 2003·Chemosphere·Karl Heinz van Pée, Susanne Unversucht
May 14, 2003·Applied Microbiology and Biotechnology·W A DuetzB Witholt
Apr 1, 2004·Chemistry : a European Journal·José BarluengaJosé M González
Sep 24, 2004·Journal of Biotechnology·Bruno Bühler, Andreas Schmid
Nov 19, 2004·Journal of the American Chemical Society·Jayme N Carter-Franklin, Alison Butler
Sep 20, 2005·Biotechnology Advances·Carla C C R de Carvalho, M Manuela R da Fonseca
Nov 9, 2005·Biotechnology and Bioengineering·Jin-Byung Park, Douglas S Clark

Citations

Dec 20, 2016·Current Opinion in Chemical Biology·Yonghua WangFrank Hollmann
May 27, 2017·Chemical Communications : Chem Comm·Jia Jia DongFrank Hollmann
Jun 7, 2014·Chemical Communications : Chem Comm·Dirk HoltmannFrank Hollmann
Nov 4, 2009·Chemical Communications : Chem Comm·Daniel I PerezFrank Hollmann
Oct 11, 2019·Organic & Biomolecular Chemistry·Georg T HöflerFrank Hollmann

Related Concepts

Cochliobolus
Bromides
Chloride Peroxidase
Chloride Ion Level
Oxydol
Iodides
In Vivo NMR Spectroscopy
Oxidation-Reduction
Molecular Stereochemistry
Substrate Specificity

Trending Feeds

COVID-19

Coronaviruses encompass a large family of viruses that cause the common cold as well as more serious diseases, such as the ongoing outbreak of coronavirus disease 2019 (COVID-19; formally known as 2019-nCoV). Coronaviruses can spread from animals to humans; symptoms include fever, cough, shortness of breath, and breathing difficulties; in more severe cases, infection can lead to death. This feed covers recent research on COVID-19.

Systemic Juvenile Idiopathic Arthritis

Systemic juvenile idiopathic arthritis is a rare rheumatic disease that affects children. Symptoms include joint pain, as well as fevers and skin rashes. Here is the latest research on this disease.

Chronic Fatigue Syndrome

Chronic fatigue syndrome is a disease characterized by unexplained disabling fatigue; the pathology of which is incompletely understood. Discover the latest research on chronic fatigue syndrome here.

Cell Atlas Along the Gut-Brain Axis

Profiling cells along the gut-brain axis at the single cell level will provide unique information for each cell type, a three-dimensional map of how cell types work together to form tissues, and insights into how changes in the map underlie health and disease of the GI system and its crosstalk with the brain. Disocver the latest research on single cell analysis of the gut-brain axis here.

Myocardial Stunning

Myocardial stunning is a mechanical dysfunction that persists after reperfusion of previously ischemic tissue in the absence of irreversible damage including myocardial necrosis. Here is the latest research.

Pontocerebellar Hypoplasia

Pontocerebellar hypoplasias are a group of neurodegenerative autosomal recessive disorders with prenatal onset, atrophy or hypoplasia of the cerebellum, hypoplasia of the ventral pons, microcephaly, variable neocortical atrophy and severe mental and motor impairments. Here is the latest research on pontocerebellar hypoplasia.

Central Pontine Myelinolysis

Central Pontine Myelinolysis is a neurologic disorder caused most frequently by rapid correction of hyponatremia and is characterized by demyelination that affects the central portion of the base of the pons. Here is the latest research on this disease.

Trichotillomania

Trichotillomania is an impulse control disorder characterized by the recurrent pulling of one's hair resulting in noticeable hair loss. Here are the latest discoveries in this field.

DDX3X Syndrome

DDX3X syndrome is caused by a spontaneous mutation at conception that primarily affects females due to its location on the X-chromosome. DDX3X syndrome has been linked to intellectual disabilities, seizures, autism, low muscle tone, brain abnormalities, and slower physical developments. Here is the latest research.