Enantiomeric excesses in meteoritic amino acids.
Gas chromatographic-mass spectral analyses of the four stereoisomers of 2-amino-2,3-dimethylpentanoic acid (dl-alpha-methylisoleucine and dl-alpha-methylalloisoleucine) obtained from the Murchison meteorite show that the L enantiomer occurs in excess (7.0 and 9.1%, respectively) in both of the enantiomeric pairs. Similar results were obtained for two other alpha-methyl amino acids, isovaline and alpha-methylnorvaline, although the alpha hydrogen analogs of these amino acids, alpha-amino-n-butyric acid and norvaline, were found to be racemates. With the exception of alpha-amino-n-butyric acid, these amino acids are either unknown or of limited occurrence in the biosphere. Because carbonaceous chondrites formed 4.5 billion years ago, the results are indicative of an asymmetric influence on organic chemical evolution before the origin of life.
Cronin
J R
JR
Department of Chemistry and Biochemistry, Arizona State University, Tempe, AZ 85287-1604, USA.
Pizzarello
S
S
D000596:Amino Acids / Q000737:chemistry*; D000613:Aminobutyrates / Q000737:chemistry; D019418:Evolution, Chemical; D018559:Exobiology; D005118:Extraterrestrial Environment; D008401:Gas Chromatography-Mass Spectrometry; D007536:Isomerism; D019110:Meteoroids; D000069497:Origin of Life; D013237:Stereoisomerism; D014633:Valine / Q000031:analogs & derivatives / Q000737:chemistry
C104341:2-amino-2,3-dimethylpentanoic acid; D000596:Amino Acids; D000613:Aminobutyrates; C104340:2-methylnorvaline; C032737:isovaline; D014633:Valine