2012
DOI: 10.1002/chem.201200466
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On the Prebiotic Synthesis of D‐Sugars Catalyzed by L‐Peptides: Assessments from First‐Principles Calculations

Abstract: What accounts for a particular chiral selection in the case of a few sugars of prebiotic relevance, thereby mirroring the asymmetry observed in nature? By using first-principles calculations, the generation of pentoses from glycolaldehyde (the initial product of the autocatalytic formose reaction), which has been detected in outer space), has been modeled by using L-Val-L-Val as a primeval catalyst. Our theoretical study provides insight into the mechanism of this reaction and satisfactorily explains a few key… Show more

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Cited by 4 publications
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“…To elucidate the subtle balance between intramolecular and two different kinds of intermolecular hydrogen bonding, it makes sense to study the simplest prototype,11 which has even been detected in interstellar space:12, 13 glycolaldehyde (CH(O)CH 2 OH). Aldol reactions of glycolaldehyde catalyzed by dipeptides can lead to pentose sugars in an enantioselective way,14 adding to the importance of glycolaldehyde in prebiotic chemistry. In solid form, glycolaldehyde adopts a cyclic dimeric hemiacetal arrangement,15, 16 but in the gas phase, it provides the two essential functional groups for this study, a hydroxy group directly neighboring a carbonyl group, with which it can form a relatively strong internal hydrogen bond 17–20.…”
Section: Introductionmentioning
confidence: 99%
“…To elucidate the subtle balance between intramolecular and two different kinds of intermolecular hydrogen bonding, it makes sense to study the simplest prototype,11 which has even been detected in interstellar space:12, 13 glycolaldehyde (CH(O)CH 2 OH). Aldol reactions of glycolaldehyde catalyzed by dipeptides can lead to pentose sugars in an enantioselective way,14 adding to the importance of glycolaldehyde in prebiotic chemistry. In solid form, glycolaldehyde adopts a cyclic dimeric hemiacetal arrangement,15, 16 but in the gas phase, it provides the two essential functional groups for this study, a hydroxy group directly neighboring a carbonyl group, with which it can form a relatively strong internal hydrogen bond 17–20.…”
Section: Introductionmentioning
confidence: 99%