apiose

{{chembox

| Watchedfields = changed

| verifiedrevid = 433741882

| Name = Apiose

| ImageFile = D-Apiose structure.svg

| ImageSize = 150px

| ImageName = Chemical structure of apiose

| IUPACName = 2,3,4-Trihydroxy-3-(hydroxymethyl)butanal

| OtherNames = {{ubl|D-Apiose
3-C-(Hydroxymethyl)-D-glycerotetrose|Apio-β-D-furanose|3-C-(Hydroxymethyl)-glycero-tetrose}}

|Section1={{Chembox Identifiers

| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}}

| ChemSpiderID = 16735670

| InChIKey = ASNHGEVAWNWCRQ-LJJLCWGRBE

| StdInChI_Ref = {{stdinchicite|correct|chemspider}}

| StdInChI = 1S/C5H10O5/c6-1-5(9)2-10-4(8)3(5)7/h3-4,6-9H,1-2H2/t3-,4?,5+/m0/s1

| StdInChIKey_Ref = {{stdinchicite|correct|chemspider}}

| StdInChIKey = ASNHGEVAWNWCRQ-LJJLCWGRSA-N

| CASNo_Ref = {{cascite|correct|??}}

| CASNo = 639-97-4

| UNII_Ref = {{fdacite|correct|FDA}}

| UNII = E59T26TCEC

| ChEBI = 141215

| KEGG = C21040

| PubChem = 12306753

| SMILES = O[C@]1(CO)COC(O)[C@@H]1O

| 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

| MeSHName =

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|Section2={{Chembox Properties

| C=5 | H=10 | O=5

| Appearance =

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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.{{Cite journal | doi = 10.1093/glycob/cww012 | pmid = 26848180 | title = Apiose: One of nature's witty games | journal = Glycobiology | volume = 26 | issue = 5 | pages = 430–442 | year = 2016 | last1 = Pičmanová | first1 = Martina | last2 = Møller | first2 = Birger Lindberg | doi-access = free }}

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.