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

doi:10.1016/S0006-291X(83)80041-2

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

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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:: Bau, R.; Brewer, I.; Chiang, M.Y.; Fujita, S.; Hoffman, J.; Watkins, M.I.; Koetzle, T.F.

Publication Date:: Fri Sep 30 00:00:00 EDT 1983

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.

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                    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.

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                    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.

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@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}

}

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DOI: 10.1016/S0006-291X(83)80041-2

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