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

Journal Article · Sun May 01 00:00:00 EDT 1988 · Proc. Natl. Acad. Sci. U.S.A.; (United States)

DOI:https://doi.org/10.1073/pnas.85.9.2889· OSTI ID:6147001

Yuan, H S.H.; Stevens, R C; Fujita, S; Watkins, M I; Koetzle, T F; Bau, R

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.

• Research Organization: Univ. of Southern California, Los Angeles (USA)
• DOE Contract Number: AC02-76CH00016
• OSTI ID: 6147001
• Journal Information: Proc. Natl. Acad. Sci. U.S.A.; (United States), Vol. 85:9
• Country of Publication: United States
• Language: English

Related Subjects

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-)