title: Catalysis of glyceraldehyde synthesis by primary or secondary amino acids under prebiotic conditions as a function of pH.
abstract: The synthesis of an excess of D-glyceraldehyde by coupling glycolaldehyde with formaldehyde under prebiotic conditions is catalyzed by L amino acids having primary amino groups at acidic pH's, but at neutral or higher pH's they preferentially form L-glyceraldehyde. L Amino acids having secondary amino groups, such as proline, have the reverse preferences, affording excess L-glyceraldehyde at low pH but excess D-glyceraldehyde at higher pHs. Detailed mechanistic proposals make these preferences understandable. The relevance of these findings to the origin of D sugars on prebiotic Earth is described.
authors.affiliation: Columbia University, New York City, USA, rb33@columbia.edu.
authors.forename: Ronald
authors.initials: R
authors.lastname: Breslow
authors.forename: Vijayakumar
authors.initials: V
authors.lastname: Ramalingam
authors.forename: Chandrakumar
authors.initials: C
authors.lastname: Appayee
mesh_terms: D000596:Amino Acids / Q000737:chemistry*; D002384:Catalysis; D019418:Evolution, Chemical; D005985:Glyceraldehyde / Q000737:chemistry*; D006863:Hydrogen-Ion Concentration; D013237:Stereoisomerism
chemical_list: D000596:Amino Acids; D005985:Glyceraldehyde