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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
Journal Name:
Biochem. Biophys. Res. Commun.; (United States)
Additional Journal Information:
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. https://doi.org/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. https://doi.org/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},
url = {https://www.osti.gov/biblio/5152030}, journal = {Biochem. Biophys. Res. Commun.; (United States)},
number = ,
volume = 115:3,
place = {United States},
year = {1983},
month = {9}
}