3-Dehydroquinic acid

In this article, we are going to delve into the fascinating world of 3-Dehydroquinic acid. From its origins to its current evolution, through its multiple facets and applications in different contexts, we will immerse ourselves in a detailed journey that will allow us to fully understand its importance and impact on society. 3-Dehydroquinic acid is a topic that has aroused the interest of many over time, and in this article we will explore its most relevant aspects, discover its possible future implications and analyze its relevance in today's world. It doesn't matter if you are an expert in the subject or if you are just beginning to delve into it, this article will provide you with valuable information and invite you to delve deeper into the exciting universe of 3-Dehydroquinic acid.
3-Dehydroquinic acid
3-Dehydroquinic acid
3-Dehydroquinic acid
Names
Preferred IUPAC name
(1R,3R,4S)-1,3,4-Trihydroxy-5-oxocyclohexane-1-carboxylic acid
Identifiers
3D model (JSmol)
ChEBI
ChemSpider
UNII
  • InChI=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 ☒N
    Key: WVMWZWGZRAXUBK-SYTVJDICSA-N ☒N
  • 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
    Key: WVMWZWGZRAXUBK-SYTVJDICBW
  • O=C1C(O)((O)=O)C(O)1O
  • O=C1(O)(O)C(O)(C(=O)O)C1
Properties
C7H10O6
Molar mass 190.152 g/mol
Except where otherwise noted, data are given for materials in their standard state (at 25 °C , 100 kPa).
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3-Dehydroquinic acid (DHQ) is the first carbocyclic intermediate of the shikimate pathway.[1] 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:

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.[2] This compound is oxidized by FAD to PQQ.

References

  1. ^ Morrow, Gary W. (2016). "The Shikimate Pathway: Biosynthesis of Phenolic Products from Shikimic Acid". Oxford University Press. doi:10.1093/oso/9780199860531.001.0001. ISBN 978-0-19-986053-1. Retrieved 2022-09-14.
  2. ^ Peón, Antonio; Otero, José M.; Tizón, Lorena; Prazeres, Verónica F. V.; Llamas-Saiz, Antonio L.; Fox, Gavin C.; van Raaij, Mark J.; Lamb, Heather; Hawkins, Alastair R.; Gago, Federico; Castedo, Luis; González-Bello, Concepción (2010-09-02). "Understanding the Key Factors that Control the Inhibition of Type II Dehydroquinase by (2R)-2-Benzyl-3-dehydroquinic Acids". ChemMedChem. 5 (10): 1726–1733. doi:10.1002/cmdc.201000281. PMID 20815012. S2CID 13587154.
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