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Prebiotic access to enantioenriched glyceraldehyde mediated by peptides.

ABSTRACT: A prebiotically plausible route to enantioenriched glyceraldehyde is reported via a kinetic resolution mediated by peptides. The reaction proceeds via a selective reaction between the l-peptide and the l-sugar producing an Amadori rearrangement byproduct and leaving d-glyceraldehyde in excess. Solubility considerations in the synthesis of proline-valine (pro-val) peptides allow nearly enantiopure pro-val to be formed starting from racemic pro and nearly racemic (10%) ee val. (ee = enantiomeric excess = (|d - l|)/(d + l)) Thus enantioenrichment of glyceraldehyde is achieved in a system with minimal initial chiral bias. This work demonstrates synergy between amino acids and sugars in the emergence of biological homochirality.

SUBMITTER: Yu J

PROVIDER: S-EPMC8115318 | biostudies-literature | 2021 Mar

REPOSITORIES: biostudies-literature

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Prebiotic access to enantioenriched glyceraldehyde mediated by peptides.

Yu Jinhan J Jones Alexander X AX Legnani Luca L Blackmond Donna G DG

Chemical science 20210331 18

A prebiotically plausible route to enantioenriched glyceraldehyde is reported <i>via</i> a kinetic resolution mediated by peptides. The reaction proceeds <i>via</i> a selective reaction between the l-peptide and the l-sugar producing an Amadori rearrangement byproduct and leaving d-glyceraldehyde in excess. Solubility considerations in the synthesis of proline-valine (pro-val) peptides allow nearly enantiopure pro-val to be formed starting from racemic pro and nearly racemic (10%) ee val. (ee = ...[more]

PMID: 34084433

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