The Strecker synthesis as a source of amino acids in carbonaceous chondrites:  deuterium retention during synthesis.
Deuterium-enriched amino acids occur in the Murchison carbonaceous chondrite. Synthesis from D-enriched interstellar precursors by Strecker reactions during aqueous alteration of the parent body has been proposed. To test this hypothesis, we have measured the retention of deuterium in amino acids produced from HCN, NH3, and formaldehyde-D2, acetaldehyde-D4, and acetone-D6 in H2O. The isotopic label is 50% to 98% retained, with variations in retentivity depending on the amino acid and the reaction conditions. If amino acids, once formed on the parent body by the Strecker synthesis, lose no deuterium by subsequent exchange with water or H-bearing minerals, then the observed deuterium isotopic composition of Murchison amino acids represents as much as 50% or more of the enrichments inherited from their interstellar precursors. Imino diacids are prominent side products of the Strecker synthesis which have not been reported in carbonaceous chondrites. Under the conditions of the Strecker reaction using deuterium labeled aldehydes and ketones, unlabeled amino acids are also formed by an HCN polymerization route indicating multiple pathways for the synthesis of amino acids in meteorites.
Lerner
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NR
Planetary Biology Branch, NASA-Ames Research Center, Moffett Field, CA 94035, USA.
Peterson
E
E
Chang
S
S
D000079:Acetaldehyde / Q000737:chemistry; D000096:Acetone / Q000737:chemistry; D000596:Amino Acids / Q000138:chemical synthesis*; D000641:Ammonia / Q000737:chemistry; D002625:Chemistry, Organic / Q000379:methods; D003903:Deuterium / Q000737:chemistry*; D005557:Formaldehyde / Q000737:chemistry; D008401:Gas Chromatography-Mass Spectrometry; D006856:Hydrogen Cyanide / Q000737:chemistry; D007098:Imino Acids / Q000138:chemical synthesis*; D007554:Isotopes; D019110:Meteoroids
D000596:Amino Acids; D007098:Imino Acids; D007554:Isotopes; D000096:Acetone; D005557:Formaldehyde; D006856:Hydrogen Cyanide; D000641:Ammonia; D003903:Deuterium; D000079:Acetaldehyde