Xylonic acid

d-Xylonic acid

Names
IUPAC name (2R,3S,4R)-2,3,4,5-tetrahydroxypentanoic acid
Other names d-Xylonic acid d-xylo-Pentonic acid
Identifiers
CAS Number	17828-56-7 (d/l) Y 526-91-0 (d) N 4172-44-5 (l>) N
3D model (JSmol)	Interactive image
ChEBI	CHEBI:48093 (d) CHEBI:48092 (l)
ChemSpider	5034782  N
PubChem CID	6602431
UNII	OCI0V55QO1  Y
CompTox Dashboard (EPA)	DTXSID701028292
InChI InChI=1S/C5H10O6/c6-1-2(7)3(8)4(9)5(10)11/h2-4,6-9H,1H2,(H,10,11)/t2-,3+,4-/m1/s1 N Key: QXKAIJAYHKCRRA-FLRLBIABSA-N N InChI=1/C5H10O6/c6-1-2(7)3(8)4(9)5(10)11/h2-4,6-9H,1H2,(H,10,11)/t2-,3+,4-/m1/s1 Key: QXKAIJAYHKCRRA-FLRLBIABBX
SMILES C([C@H]([C@@H]([C@H](C(=O)O)O)O)O)O
Properties
Chemical formula	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). N  verify  (what is  YN ?) Infobox references

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

1. 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.
2. 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.