Chiral Sugars Drive Enantioenrichment in Prebiotic
Amino Acid Synthesis
Version 3 2017-04-26, 05:20
Version 2 2017-03-21, 17:03
Version 1 2017-03-21, 16:34
Posted on 2017-04-26 - 05:20
Chiral pentose sugars
mediate the enantioselective synthesis of
amino acid precursors, with the magnitude of the chiral induction
dictated by a subtle cooperativity between sugar hydroxyl groups.
Ribose and lyxose give opposite chiral preferences, and theoretical
calculations reveal the pseudoenantiomeric nature of transition state
structures from the two sugars. Prebiotically plausible mixtures of
natural d-sugars lead to enantioenrichment of natural l-amino acid precursors. Temporal monitoring and kinetic modeling
of the reaction reveal an unusual dynamic kinetic resolution that
shifts toward an enantioselective pathway over time, providing an
amplification mechanism for the transfer of chiral information. This
work adds to growing evidence for synergy in the etiology of the single
chirality of the two most important classes of biological molecules,
the sugars that make up DNA and RNA and the amino acids that form
proteins.
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Wagner, Alexander
J.; Zubarev, Dmitry Yu.; Aspuru-Guzik, Alán; Blackmond, Donna G. (2017). Chiral Sugars Drive Enantioenrichment in Prebiotic
Amino Acid Synthesis. ACS Publications. Collection. https://doi.org/10.1021/acscentsci.7b00085
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AUTHORS (4)
AW
Alexander
J. Wagner
DZ
Dmitry Yu. Zubarev
AA
Alán Aspuru-Guzik
DB
Donna G. Blackmond
KEYWORDS
Chiral Sugars Drive Enantioenrichmentamplification mechanismchiral informationform proteinsl-amino acid precursorschiral preferencesPrebiotic Aminosugar hydroxyl groupsenantioselective pathwayenantioselective synthesischiral inductionDNATemporal monitoringpseudoenantiomeric natureSynthesis Chiral pentose sugarsRNAacid precursorstransition state structures