Xylonic acid
Appearance
Names | |
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IUPAC name
(2R,3S,4R)-2,3,4,5-tetrahydroxypentanoic acid
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Other names
Xylonate
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Identifiers | |
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3D model (JSmol)
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ChEBI |
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ChemSpider | |
PubChem CID
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UNII | |
CompTox Dashboard (EPA)
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Properties | |
C 5H 10O 6 | |
Molar mass | 166.13 g/mol |
Appearance | white solid |
Melting point | 120–122 °C (248–252 °F; 393–395 K) |
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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Xylonic acid is the organic compound with the formula HOCH2CH(OH)CH(OH)CH(OH)CO2H. It is an oxidized derivative of xylose. Xylonic acid is a colorless, water-soluble solid. Several isomers are known, all being classified as sugar acids, several of which can be obtained by oxidation of the corresponding pentoses. The C-2 epimer of xylonic acid is known as lyxonic acid.
Like other sugar acids, xylonic acid readily converts to a lactone (RN 15384-37-9) by dehydration. Lyxonic acid behaves similarly.
Genetically engineered Pseudomonas fragi converts D-xylose to D-xylonic acid. Decarboxylation of the xylonic acid by a strain of Escherichia coli give [[1,2,4-Butanetriol|1,2,4-butanetriol], which is of commercial interest.[1][2]
References
[edit]- ^ Niu, W.; Molefe, M. N.; Frost, J. W. (2003). "Microbial synthesis of the energetic material precursor 1,2,4-butanetriol". Journal of the American Chemical Society. 125 (43): 12998–12999. doi:10.1021/ja036391. PMID 14570452.
- ^ Francois, Jean Marie; Alkim, Ceren; Morin, Nicolas (2020). "Engineering Microbial Pathways for Production of Bio-based Chemicals from Lignocellulosic Sugars: Current Status and Perspectives". Biotechnology for Biofuels. 13: 118. doi:10.1186/s13068-020-01744-6. PMC 7341569. PMID 32670405.