The peptide-catalyzed stereospecific synthesis of tetroses: a possible model for prebiotic molecular evolution.

Abstract:

:Using a water-based prebiotic model of sugar synthesis involving glycolaldehyde self-condensation, we demonstrate that homochiral L-dipeptide catalysts lead to the stereospecific syntheses of tetroses. The asymmetric effect is largest for erythrose, which may reach a D-enantiomeric excess of >80% with L-Val-L-Val catalyst. Based on results obtained with various peptides, we propose a possible catalytic-reaction intermediate, consisting of an imidazolidinone ring formed between the two nitrogen atoms of the peptide catalyst and the C1 of one glycolaldehyde molecule. The study was motivated by the premise that exogenous material, such as the nonracemic amino acids found in meteorites, could have participated in the terrestrial evolution of molecular asymmetry by stereospecific catalysis. Because peptides might have formed readily on the early Earth, it is possible that their catalytic contribution was relevant in the prebiotic processes that preceded the onset of life.

authors

Weber AL,Pizzarello S

doi

10.1073/pnas.0602320103

subject

Has Abstract

pub_date

2006-08-22 00:00:00

pages

12713-7

issue

34

eissn

0027-8424

issn

1091-6490

pii

0602320103

journal_volume

103

pub_type

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