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Title: Absolute configuration of a chiral CHD group via neutron diffraction: confirmation of the absolute stereochemistry of the enzymatic formation of malic acid

Abstract

Neutron diffraction has been used to monitor the absolute stereochemistry of an enzymatic reaction. (-)(2S)malic-3-d acid was prepared by the action of fumarase on fumaric acid in D/sub 2/O. After a large number of cations were screened, it was found that (+)(R)..cap alpha..-phenylethylamine forms the large crystals necessary for a neutron diffraction analysis. The subsequent structure determination showed that (+)(R)..cap alpha..-phenylethylammonium (-)(2S)malate-3-d has an absolute configuration of R at the CHD site. This result confirms the absolute stereochemistry of fumarate-to-malate transformation as catalyzed by the enzyme fumarase.

Authors:
; ; ; ; ; ;
Publication Date:
Research Org.:
Univ. of Southern California, Los Angeles
OSTI Identifier:
5152030
Resource Type:
Journal Article
Resource Relation:
Journal Name: Biochem. Biophys. Res. Commun.; (United States); Journal Volume: 115:3
Country of Publication:
United States
Language:
English
Subject:
59 BASIC BIOLOGICAL SCIENCES; HYDRO-LYASES; BIOCHEMICAL REACTION KINETICS; STEREOCHEMISTRY; MALIC ACID; CRYSTALLIZATION; DERIVATIZATION; NEUTRON DIFFRACTION; AMINES; FUMARIC ACID; HEAVY WATER; KREBS CYCLE; LABELLING; CARBON-OXYGEN LYASES; CARBOXYLIC ACIDS; CHEMICAL REACTIONS; COHERENT SCATTERING; DICARBOXYLIC ACIDS; DIFFRACTION; ENZYMES; HYDROGEN COMPOUNDS; HYDROXY ACIDS; KINETICS; LYASES; ORGANIC ACIDS; ORGANIC COMPOUNDS; OXYGEN COMPOUNDS; PHASE TRANSFORMATIONS; REACTION KINETICS; SCATTERING; WATER; 550200* - Biochemistry

Citation Formats

Bau, R., Brewer, I., Chiang, M.Y., Fujita, S., Hoffman, J., Watkins, M.I., and Koetzle, T.F. Absolute configuration of a chiral CHD group via neutron diffraction: confirmation of the absolute stereochemistry of the enzymatic formation of malic acid. United States: N. p., 1983. Web. doi:10.1016/S0006-291X(83)80041-2.
Bau, R., Brewer, I., Chiang, M.Y., Fujita, S., Hoffman, J., Watkins, M.I., & Koetzle, T.F. Absolute configuration of a chiral CHD group via neutron diffraction: confirmation of the absolute stereochemistry of the enzymatic formation of malic acid. United States. doi:10.1016/S0006-291X(83)80041-2.
Bau, R., Brewer, I., Chiang, M.Y., Fujita, S., Hoffman, J., Watkins, M.I., and Koetzle, T.F. Fri . "Absolute configuration of a chiral CHD group via neutron diffraction: confirmation of the absolute stereochemistry of the enzymatic formation of malic acid". United States. doi:10.1016/S0006-291X(83)80041-2.
@article{osti_5152030,
title = {Absolute configuration of a chiral CHD group via neutron diffraction: confirmation of the absolute stereochemistry of the enzymatic formation of malic acid},
author = {Bau, R. and Brewer, I. and Chiang, M.Y. and Fujita, S. and Hoffman, J. and Watkins, M.I. and Koetzle, T.F.},
abstractNote = {Neutron diffraction has been used to monitor the absolute stereochemistry of an enzymatic reaction. (-)(2S)malic-3-d acid was prepared by the action of fumarase on fumaric acid in D/sub 2/O. After a large number of cations were screened, it was found that (+)(R)..cap alpha..-phenylethylamine forms the large crystals necessary for a neutron diffraction analysis. The subsequent structure determination showed that (+)(R)..cap alpha..-phenylethylammonium (-)(2S)malate-3-d has an absolute configuration of R at the CHD site. This result confirms the absolute stereochemistry of fumarate-to-malate transformation as catalyzed by the enzyme fumarase.},
doi = {10.1016/S0006-291X(83)80041-2},
journal = {Biochem. Biophys. Res. Commun.; (United States)},
number = ,
volume = 115:3,
place = {United States},
year = {Fri Sep 30 00:00:00 EDT 1983},
month = {Fri Sep 30 00:00:00 EDT 1983}
}