3-Dehydroquinic acid: Difference between revisions
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! {{chembox header}}| '''3-Dehydroquinic acid''' <!-- replace if not identical with the article name --> |
! {{chembox header}}| '''3-Dehydroquinic acid''' <!-- replace if not identical with the article name --> |
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| align="center" colspan="2" bgcolor="#ffffff" | [[Image:3-dehydroquinic-acid-Line-Structure.png|200px|3-Dehydroquinic acid]] |
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| [[IUPAC nomenclature|Systematic name]] |
| [[IUPAC nomenclature|Systematic name]] |
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| (1R,3R,4S)-1,3,4-trihydroxy-5-oxocyclohexanecarboxylic acid |
| (1R,3R,4S)-1,3,4-trihydroxy-<br\>5-oxocyclohexanecarboxylic acid |
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| [[Chemical formula]] |
| [[Chemical formula]] |
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| [[Simplified molecular input line entry specification|SMILES]] |
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| <small>O=C1C[C@@](O)([C@@](O)=O)C[C@@H](O)[C@@H]1O</small> |
| <small>O=C1C[C@@](O)([C@@](O)=O)C[C@@H]<br\>(O)[C@@H]1O</small> |
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| {{chembox header}} | <small>[[wikipedia:Chemical infobox|Disclaimer and references]]</small> |
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Revision as of 02:29, 15 August 2006
| 3-Dehydroquinic acid | |
|---|---|
| 3-Dehydroquinic acid | |
| Systematic name | (1R,3R,4S)-1,3,4-trihydroxy-<br\>5-oxocyclohexanecarboxylic acid |
| Chemical formula | C7H10O6 |
| Molecular mass | 190.152 g/mol |
| Density | x.xxx g/cm3 |
| Melting point | xx.x °C |
| Boiling point | xx.x °C |
| CAS number | [xx-xx-xx] |
| SMILES | O=C1C[C@@](O)([C@@](O)=O)C[C@@H]<br\>(O)[C@@H]1O |
| 3-Dehydroquinic acid | |
| 3-Dehydroquinic acid | |
| Disclaimer and references | |
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.