“3-Dehydroquinic acid”的意思、由来-开放百科全书

词条

3-Dehydroquinic acid

释义

Biosynthesis
References

{{Redirect-synonym|DHQ|Digital Humanities Quarterly}}{{chembox
| Verifiedfields = changed
| Watchedfields = changed
| verifiedrevid = 477218283
| Name = 3-Dehydroquinic acid
| ImageFile = 3-dehydroquinic-acid-Line-Structure.svg
| ImageSize = 200px
| ImageName = 3-Dehydroquinic acid
| IUPACName = (1R,3R,4S)-1,3,4-trihydroxy-5-oxocyclohexanecarboxylic acid
| Section1 = {{Chembox Identifiers
| ChemSpiderID_Ref = {{chemspidercite|changed|chemspider}}
| ChemSpiderID = 388474
| InChI = 1/C7H10O6/c8-3-1-7(13,6(11)12)2-4(9)5(3)10/h3,5,8,10,13H,1-2H2,(H,11,12)/t3-,5+,7-/m1/s1
| InChIKey = WVMWZWGZRAXUBK-SYTVJDICBW
| SMILES1 = O=C1[C@@H](O)[C@H](O)C[C@](O)(C(=O)O)C1
| StdInChI_Ref = {{stdinchicite|changed|chemspider}}
| StdInChI = 1S/C7H10O6/c8-3-1-7(13,6(11)12)2-4(9)5(3)10/h3,5,8,10,13H,1-2H2,(H,11,12)/t3-,5+,7-/m1/s1
| StdInChIKey_Ref = {{stdinchicite|changed|chemspider}}
| StdInChIKey = WVMWZWGZRAXUBK-SYTVJDICSA-N
| CASNo_Ref = {{cascite|changed|??}}
| CASNo = 10534-44-8
| PubChem = 439351
| ChEBI_Ref = {{ebicite|changed|EBI}}
| ChEBI = 17947
| SMILES = O=C1C[C@@](O)([C@@](O)=O)C[C@@H](O)[C@@H]1O
| Section2 = {{Chembox Properties
| Formula = C₇H₁₀O₆
| MolarMass = 190.152 g/mol
| Density =
| MeltingPt =
| BoilingPt =
}}

3-Dehydroquinic acid (DHQ) is the first carbocyclic intermediate of the shikimate pathway. It is created from 3-deoxyarabinoheptulosonate 7-phosphate, a 7-carbon ulonic acid, by the enzyme DHQ synthase. The mechanism of ring closure is complex, but involves an aldol condensation at C-2 and C-7.

It has the same structure as quinic acid, which is found in coffee, but the C-3 hydroxyl is oxidized to a ketone group. 3-Dehydroquinic acid undergoes five further enzymatic steps in the remainder of the shikimate pathway to chorismic acid, a precursor to tyrosine, 3-phenylalanine, tryptophan, and some vitamins, including:

Vitamin K
Pteroylmonoglutamic acid, called folate.

3-Dehydroquinate can also be a precursor to pyrroloquinoline quinone (PQQ), an alternate redox coenzyme involved in oxidative phosphorylation.

Biosynthesis

3-Dehydroquinate goes through beta oxidation, similar to fatty acids. Then, this compound (6-oxo-3-dehydro-quinate) is transaminated to 6-amino-3-dehydroquinate. Then 6-amino-3-dehydro-quinate is dehydrated and reduced to 6-amino-4-desoxy-3-keto-quinate, which reacts with dehydroalanine and alpha-ketoglutarate, to form hexahydro-pyrroloquinoline quinone. This compound is oxidized by FAD to PQQ.

References

3 : Hydroxy acids|Ketones|Cyclohexanols

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