Journal
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY
Volume 134, Issue 7, Pages 3577-3589Publisher
AMER CHEMICAL SOC
DOI: 10.1021/ja211383c
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Funding
- Skaggs Research Foundation
- NASA [NNX09AM96G]
- NSF
- NASA under the NSF Center for Chemical Evolution [CHE-1004570]
- NASA [113611, NNX09AM96G] Funding Source: Federal RePORTER
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In the context of a glyoxylate scenario of primordial metabolism,(1) the reactions of dihydroxyfumarate (DHF) with reactive small molecule aldehydes (e.g., glyoxylate, formaldehyde, glycolaldehyde, and glyceraldehyde) in water were investigated and shown to form dihydroxyacetone, tetrulose, and the two pentuloses, with almost quantitative conversion. The practically clean and selective formation of ketoses in these reactions, with no detectable admixture of aldoses, stands in stark contrast to the formose reaction, where a complex mixture of linear and branched aldoses and ketoses are produced. These results suggest that the reaction of DHF with aldehydes could constitute a reasonable pathway for the formation of carbohydrates and allow for alternative potential prebiotic scenarios to the formose reaction to be considered.
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