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5-Deoxyinositol


5-Deoxyinositol (quercitol) is a cyclitol. It can be found in wines aged in oak wood barrels. It can also be found in Quercus sp. (oaks) and in Gymnema sylvestre. It is different from , a synonym of quercetin.

Biosynthesis

The proposed biosynthesis of 5-deoxyinositol begins with the conversion of D-glucose to myo-inositol. In this pathway, D-glucose is phosphorylated to form D-glucose-6-phosphate. The NAD+ dependent enzyme inositol 1-phosphate synthase (I1PS) then catalyzes the subsequent oxidation, enolization, aldol cyclization, and reduction of D-glucose 6-phosphate to form myo-inositol 1-phosphate. Hydrolysis of the phosphate group on this molecule gives myo-inositol. Myo-inositol can then be converted into 5-deoxyinositol in three steps, beginning with the oxidation of myo-inositol by inositol dehydrogenase (ID) to form scyllo-inosose. This intermediate is then dehydrated to form a diketone. The reduction of this diketone gives 5-deoxyinositol. This final reduction is thought to be catalyzed by one or more unidentified reductases or dehydrogenases.

:[[File:5-deoxyinositol biosynthesis.svg|thumb|left|600px|Biosynthesis of 5-deoxyinositol]]

References

References

  1. ''[[Merck Index]]'', 12th Edition, '''8218'''
  2. Davinia Carlavilla. (2006). "Occurrence and Significance of Quercitol and Other Inositols in Wines during Oak Wood Aging". Am. J. Enol. Vitic..
  3. Sonia Rodríguez-Sánchez. (2010). "Analysis of cyclitols in different Quercus species by gas chromatography–mass spectrometry". Journal of the Science of Food and Agriculture.
  4. (1997-09-04). "1L-myo-inositol-1-phosphate synthase". Biochimica et Biophysica Acta (BBA) - Lipids and Lipid Metabolism.
  5. (2008-04-18). "myo-Inositol catabolism in Bacillus subtilis". The Journal of Biological Chemistry.
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