Non-racemic amino acids in the Murray and Murchison meteorites.
Small (1.0-9.2%) L-enantiomer excesses were found in six alpha-methyl-alpha-amino alkanoic acids from the Murchison (2.8-9.2%) and Murray (1.0-6.0%) carbonaceous chondrites by gas chromatography-mass spectroscopy of their N-trifluoroacetyl or N-pentafluoropropyl isopropyl esters. These amino acids [2-amino-2,3-dimethylpentanoic acid (both diastereomers), isovaline, alpha-methyl norvaline, alpha-methyl valine, and alpha-methyl norleucine] are either unknown or rare in the terrestrial biosphere. Enantiomeric excesses were either not observed in the four alpha-H-alpha-amino alkanoic acids analyzed (alpha-amino-n-butyric acid, norvaline, alanine, and valine) or were attributed to terrestrial contamination. The substantial excess of L-alanine reported by others was not found in the alanine in fractionated extracts of either meteorite. The enantiomeric excesses reported for the alpha-methyl amino acids may be the result of partial photoresolution of racemic mixtures caused by ultraviolet circularly polarized light in the presolar cloud. The alpha-methyl-alpha-amino alkanoic acids could have been significant in the origin of terrestrial homochirality given their resistance to racemization and the possibility for amplification of their enantiomeric excesses suggested by the strong tendency of their polymers to form chiral secondary structure.
Pizzarello
S
S
Department of Chemistry and Biochemistry, Arizona State University, Tempe 85287-1604, USA. spizzarello@asu.edu
Cronin
J R
JR
D000596:Amino Acids / Q000032:analysis* / Q000737:chemistry; D019418:Evolution, Chemical; D018559:Exobiology; D005118:Extraterrestrial Environment; D008401:Gas Chromatography-Mass Spectrometry; D018535:Mars; D019110:Meteoroids; D015394:Molecular Structure; D000069497:Origin of Life; D015203:Reproducibility of Results; D013237:Stereoisomerism
D000596:Amino Acids