title: S-Isovaline Contained in Meteorites, Induces Enantiomeric Excess in D,L-glutamic Acid During Recrystallization.
abstract: S-Isovaline (S-Iva: 6.7 mmol) and D,L-glutamic acid (Glu: 2 mmol) were dissolved in 10 ml of hot water, and the resulting solution was divided in 5 vessels. After recrystallization, the crystals were collected from each vessel, and the enantiomeric excess (ee) of Glu was determined with chemical derivatization using 1-fluoro-2,4-dinitrophenyl- 5-L-leucinamide followed by high-performance liquid chromatography. Ten crystallizations provided all D-rich Glu with ee values of 2.69 % ± 0.81% (mean ± standard deviation), and those using R-Iva provided all L-rich Glu with ee values of 6.24 % ± 2.20%. Five recrystallizations of D,L-Glu alone provided ee values of 0.474 % ± 0.33%. The differences among these three ee values were statistically significant, showing that S-Iva, which was present in meteorites caused a significant induction of ee in this physiological amino acid. This is the first outcome that S-Iva induced ee changes in a physiological amino acid. S-Iva did not induce any ee changes in D,L-asparagine, leucine, valine, methionine, phenylalanine, tryptophan, glutamine, tyrosine, aspartic acid, or histidine under similar recrystallizations.
authors.affiliation: The Open University of Japan, Wakaba, Mihama, Chiba, 261-8586, Japan, kojo@ouj.ac.jp.
authors.forename: Shosuke
authors.initials: S
authors.lastname: Kojo
mesh_terms: D001216:Asparagine / Q000737:chemistry*; D002851:Chromatography, High Pressure Liquid; D003460:Crystallization; D019418:Evolution, Chemical; D018698:Glutamic Acid / Q000737:chemistry*; D007930:Leucine / Q000031:analogs & derivatives / Q000737:chemistry; D019110:Meteoroids; D009574:Nitro Compounds / Q000737:chemistry; D013237:Stereoisomerism; D014633:Valine / Q000737:chemistry*
chemical_list: C439871:1-fluoro-2,4-dinitrophenyl-5-leucinamide; D009574:Nitro Compounds; D018698:Glutamic Acid; C032737:isovaline; D001216:Asparagine; D007930:Leucine; D014633:Valine