cap alpha. -deuterium and carbon-13 isotope effects for methyl transfer catalyzed by catechol O-methyltransferase. S/sub N/2-like transition state
Journal Article
·
· J. Am. Chem. Soc.; (United States)
The rate at near saturation of methylation of 3,4-dihydroxyacetophenone by S-adenosyl-L-methionine, catalyzed by rat-liver catechol O-methyltransferase at pH 7.58 and 37.00 +- 0.05/sup 0/C, is increased by deuteration of the methyl group (V/sub CH/sub 3///V/sub CD/sub 3// = 0.83 +- 0.05) and decreased by introduction of /sup 13/C to the methyl group (V/sub 12//V/sub 13/ = 1.09 +- 0.05). This shows the rate-determining step to be transfer of the methyl group, with an S/sub N/2-like transition state in which the methyl is located symmetrically and tightly between leaving group and nucleophile.
- Research Organization:
- Univ. of Kansas, Lawrence
- OSTI ID:
- 5776917
- Journal Information:
- J. Am. Chem. Soc.; (United States), Vol. 101:15
- Country of Publication:
- United States
- Language:
- English
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Related Subjects
37 INORGANIC
ORGANIC
PHYSICAL AND ANALYTICAL CHEMISTRY
59 BASIC BIOLOGICAL SCIENCES
CARBON 13
ISOTOPE EFFECTS
DEUTERIUM
ACETOPHENONE
ADENOSINE
EXPERIMENTAL DATA
HYDROXY COMPOUNDS
ISOLATED VALUES
METHIONINE
METHYLATION
TRANSFERASES
AMINO ACIDS
CARBON ISOTOPES
CARBOXYLIC ACIDS
CHEMICAL REACTIONS
DATA
DATA FORMS
ENZYMES
EVEN-ODD NUCLEI
HYDROGEN ISOTOPES
INFORMATION
ISOTOPES
KETONES
LIGHT NUCLEI
LIPOTROPIC FACTORS
NUCLEI
NUCLEOSIDES
NUCLEOTIDES
NUMERICAL DATA
ODD-ODD NUCLEI
ORGANIC ACIDS
ORGANIC COMPOUNDS
ORGANIC SULFUR COMPOUNDS
RIBOSIDES
STABLE ISOTOPES
400302* - Organic Chemistry- Isotope Effects- (-1987)
550201 - Biochemistry- Tracer Techniques
ORGANIC
PHYSICAL AND ANALYTICAL CHEMISTRY
59 BASIC BIOLOGICAL SCIENCES
CARBON 13
ISOTOPE EFFECTS
DEUTERIUM
ACETOPHENONE
ADENOSINE
EXPERIMENTAL DATA
HYDROXY COMPOUNDS
ISOLATED VALUES
METHIONINE
METHYLATION
TRANSFERASES
AMINO ACIDS
CARBON ISOTOPES
CARBOXYLIC ACIDS
CHEMICAL REACTIONS
DATA
DATA FORMS
ENZYMES
EVEN-ODD NUCLEI
HYDROGEN ISOTOPES
INFORMATION
ISOTOPES
KETONES
LIGHT NUCLEI
LIPOTROPIC FACTORS
NUCLEI
NUCLEOSIDES
NUCLEOTIDES
NUMERICAL DATA
ODD-ODD NUCLEI
ORGANIC ACIDS
ORGANIC COMPOUNDS
ORGANIC SULFUR COMPOUNDS
RIBOSIDES
STABLE ISOTOPES
400302* - Organic Chemistry- Isotope Effects- (-1987)
550201 - Biochemistry- Tracer Techniques