Enantiomeric excesses in meteoritic amino acids

Science

Volumn 275, Issue 5302, 1997, Pages 951-955

  Cronin, John R ^a   Pizzarello, Sandra ^a  

^a ARIZONA STATE UNIVERSITY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

2 AMINOBUTYRIC ACID; ALLOISOLEUCINE; ALPHA AMINO ACID; CARBON; ISOLEUCINE; ISOVALINE; NORVALINE;

ARTICLE; ASTRONOMY; CHIRALITY; DIASTEREOISOMER; ENANTIOMER; GAS CHROMATOGRAPHY; MASS SPECTROMETRY; PRIORITY JOURNAL; RACEMIC MIXTURE; STEREOISOMERISM;

NASA DISCIPLINE EXOBIOLOGY; NASA DISCIPLINE NUMBER 52-10; NASA PROGRAM EXOBIOLOGY; NON-NASA CENTER;

AMINO ACIDS; AMINOBUTYRIC ACIDS; BIOGENESIS; EVOLUTION, CHEMICAL; EXOBIOLOGY; EXTRATERRESTRIAL ENVIRONMENT; GAS CHROMATOGRAPHY-MASS SPECTROMETRY; ISOMERISM; METEOROIDS; STEREOISOMERISM; VALINE;

AMINO ACID; CARBONACEOUS CHONDRITE; ENANTIOMER; MURCHISON METEORITE;

EID: 0030621130     PISSN: 00368075     EISSN: None     Source Type: Journal    
DOI: 10.1126/science.275.5302.951     Document Type: Article

References (45)

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28. Four amino acids were analyzed in this work in addition to the two diastereomers of 2-a-2,3-dmpa. 2-Methyl norvaline has no known natural terrestrial source. Isovaline has been found in fungal antibiotics [H. Brückner, J. Maisch, C. Reinecke, A. Kimonyo, Amino Acids 1, 251 (1991)]. Norvaline has been reported in an antifungal peptide produced by Bacillus subtilis [ P. Nandi and G. P. Sen, Nature 171, 871 (1953)] and as an isoleucine fermentation product [M. Kisumi, M. Sugiura, I. Chibata, J. Biochem. 80, 333 (1976)]. α-Amino-n-butyric acid is the most widely distributed, occurring in vertebrate physiological fluids and in plants.
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40. This result is analogous to the α-epimerization of L-isoleucine (2S,3S), which gives D-alloisoleucine (2R,3S); however, in the case of a Strecker synthesis, the 2S-2R equilibrium is achieved by formation of the chiral center rather than by inversion of the configuration at an existing chiral center. As envisioned here, the C-3 of 2-a-2,3-dmpa would not necessarily have been homochiral as in the case of biological isoleucine, but might have had only a modest enantiomeric excess. Consequently, excesses of the D and L enantiomers of the respective diastereomers would also have been small.
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45. We thank C. Moore of the Arizona State University Center for Meteorite Studies for a sample of the Murchison meteorite; M. Madison for calculation of the isomer numbers using the program ASSEMBLE [B. D. Christie and M. E. Munk, Anal. Chim. Acta 200, 347 (1987)]; R. Nieman for help in obtaining and interpreting NMR spectra; J. Bada, K. Kvenvolden, and an anonymous reviewer for constructive reviews of the manuscript; and the NASA Exobiology Program for research support (NAGW-1899).