Apiose

Apiose
Names

IUPAC name 2,3,4-Trihydroxy-3-(hydroxymethyl)butanal
Other names D-Apiose 3-C-(Hydroxymethyl)-D-glycerotetrose Apio-β-D-furanosyl
Identifiers
CAS Number	639-97-4^Y
3D model (JSmol)	Interactive image
ChEBI	CHEBI:141215
ChemSpider	16735670^Y
KEGG	C21040
PubChem CID	12306753
UNII	E59T26TCEC^Y
InChI InChI=1S/C5H10O5/c6-1-5(9)2-10-4(8)3(5)7/h3-4,6-9H,1-2H2/t3-,4?,5+/m0/s1^Y Key: ASNHGEVAWNWCRQ-LJJLCWGRSA-N^Y InChI=1/C5H10O5/c6-1-5(9)2-10-4(8)3(5)7/h3-4,6-9H,1-2H2/t3-,4?,5+/m0/s1 Key: ASNHGEVAWNWCRQ-LJJLCWGRBE
SMILES O[C@]1(CO)COC(O)[C@@H]1O
Properties
Chemical formula	C₅H₁₀O₅
Molar mass	150.130 g·mol⁻¹
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). Y verify (what is ^YN ?) Infobox references

Chemical compound

Apiose is a branched-chain sugar found as residues in galacturonans-type pectins; that occurs in parsley and many other plants. Apiose is a component of cell wall polysaccharides.^[1]

Apiose 1-reductase uses D-apiitol and NAD⁺ to produce apiitol-apiose, NADH, and H⁺.

Flavone apiosyltransferase uses UDP-apiose and 5,7,4'-trihydroxyflavone 7-O-β-D-glucoside to produce UDP, 5,7,4'-trihydroxyflavone (apigenin), and 7-O-β-D-apiosyl-(1->2)-β-apiitol-glucoside.

References

^ Pičmanová, Martina; Møller, Birger Lindberg (2016). "Apiose: One of nature's witty games". Glycobiology. 26 (5): 430–442. doi:10.1093/glycob/cww012. PMID 26848180.