skip to main content
OSTI.GOV title logo U.S. Department of Energy
Office of Scientific and Technical Information

Title: Determination of the absolute configuration of (-)-(2R)-succinic-2-d acid by neutron diffraction study: Unambiguous proof of the absolute stereochemistry of the NAD/sup +//NADH interconversion

Abstract

The absolute configuration of the CHD group (D = deuterium) in (-)-(2R)-succinic-2-d acid, as prepared from (-)-(2S,3R)-malic-3-d acid, has been shown unambiguously to be R by the technique of single-crystal neutron diffraction. The optically active cation (+)-phenylethylammonium was used as the chiral reference. The structure of (C/sub 6/H/sub 5/CH/sub 3/CHNH/sub 3/)/sup +/(HOOCCH/sub 2/CHDCOOO)/sup -/ has been studied with x-ray diffraction at room temperature and neutron diffraction at room temperature and neutron diffraction at 100 K. Crystal data from the neutron diffraction analysis of the phenylethylammonium slat of the title compound at 100 K: space group P2/sub 1/; a = 8.407 /angstrom/, b = 8.300 /angstrom/, c = 8.614 /angstrom/, ..beta.. = 91.20/degrees/; unit cell volume = 600.9 /angstrom//sup 3/, Z = 2. The result confirms the stereochemistry of the malate/succinate transformation, as well as the NAD/sup +//NADH interconversion, and demonstrates the usefulness of the single-crystal neutron diffraction method for determining the absolute configuration of molecules having a chiral monodeuteriomethylene group.

Authors:
; ; ; ; ;
Publication Date:
Research Org.:
Univ. of Southern California, Los Angeles (USA)
OSTI Identifier:
6147001
DOE Contract Number:  
AC02-76CH00016
Resource Type:
Journal Article
Journal Name:
Proc. Natl. Acad. Sci. U.S.A.; (United States)
Additional Journal Information:
Journal Volume: 85:9
Country of Publication:
United States
Language:
English
Subject:
62 RADIOLOGY AND NUCLEAR MEDICINE; NAD; STEREOCHEMISTRY; SUCCINIC ACID; NEUTRON DIFFRACTION; CATIONS; CRYSTALLOGRAPHY; DEUTERIUM COMPOUNDS; X-RAY DIFFRACTION; CARBOXYLIC ACIDS; CHARGED PARTICLES; COENZYMES; COHERENT SCATTERING; DICARBOXYLIC ACIDS; DIFFRACTION; HYDROGEN COMPOUNDS; IONS; NUCLEOTIDES; ORGANIC ACIDS; ORGANIC COMPOUNDS; SCATTERING; 550602* - Medicine- External Radiation in Diagnostics- (1980-)

Citation Formats

Yuan, H S.H., Stevens, R C, Fujita, S, Watkins, M I, Koetzle, T F, and Bau, R. Determination of the absolute configuration of (-)-(2R)-succinic-2-d acid by neutron diffraction study: Unambiguous proof of the absolute stereochemistry of the NAD/sup +//NADH interconversion. United States: N. p., 1988. Web. doi:10.1073/pnas.85.9.2889.
Yuan, H S.H., Stevens, R C, Fujita, S, Watkins, M I, Koetzle, T F, & Bau, R. Determination of the absolute configuration of (-)-(2R)-succinic-2-d acid by neutron diffraction study: Unambiguous proof of the absolute stereochemistry of the NAD/sup +//NADH interconversion. United States. doi:10.1073/pnas.85.9.2889.
Yuan, H S.H., Stevens, R C, Fujita, S, Watkins, M I, Koetzle, T F, and Bau, R. Sun . "Determination of the absolute configuration of (-)-(2R)-succinic-2-d acid by neutron diffraction study: Unambiguous proof of the absolute stereochemistry of the NAD/sup +//NADH interconversion". United States. doi:10.1073/pnas.85.9.2889.
@article{osti_6147001,
title = {Determination of the absolute configuration of (-)-(2R)-succinic-2-d acid by neutron diffraction study: Unambiguous proof of the absolute stereochemistry of the NAD/sup +//NADH interconversion},
author = {Yuan, H S.H. and Stevens, R C and Fujita, S and Watkins, M I and Koetzle, T F and Bau, R},
abstractNote = {The absolute configuration of the CHD group (D = deuterium) in (-)-(2R)-succinic-2-d acid, as prepared from (-)-(2S,3R)-malic-3-d acid, has been shown unambiguously to be R by the technique of single-crystal neutron diffraction. The optically active cation (+)-phenylethylammonium was used as the chiral reference. The structure of (C/sub 6/H/sub 5/CH/sub 3/CHNH/sub 3/)/sup +/(HOOCCH/sub 2/CHDCOOO)/sup -/ has been studied with x-ray diffraction at room temperature and neutron diffraction at room temperature and neutron diffraction at 100 K. Crystal data from the neutron diffraction analysis of the phenylethylammonium slat of the title compound at 100 K: space group P2/sub 1/; a = 8.407 /angstrom/, b = 8.300 /angstrom/, c = 8.614 /angstrom/, ..beta.. = 91.20/degrees/; unit cell volume = 600.9 /angstrom//sup 3/, Z = 2. The result confirms the stereochemistry of the malate/succinate transformation, as well as the NAD/sup +//NADH interconversion, and demonstrates the usefulness of the single-crystal neutron diffraction method for determining the absolute configuration of molecules having a chiral monodeuteriomethylene group.},
doi = {10.1073/pnas.85.9.2889},
journal = {Proc. Natl. Acad. Sci. U.S.A.; (United States)},
number = ,
volume = 85:9,
place = {United States},
year = {1988},
month = {5}
}