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出典(authority):フリー百科事典『ウィキペディア（Wikipedia）』「2016/07/19 04:45:12」(JST)
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Galactitol
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| Names |
| IUPAC name
(2R,3S,4R,5S)-hexane-1,2,3,4,5,6-hexol
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| Other names
D-Galactitol; Dulcitol
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| Identifiers |
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CAS Number
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608-66-2 Y |
| ChEBI |
CHEBI:16813 Y |
| ChEMBL |
ChEMBL1773904 N |
| ChemSpider |
11357 Y |
| Jmol 3D model |
Interactive image |
| PubChem |
11850 |
InChI
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InChI=1S/C6H14O6/c7-1-3(9)5(11)6(12)4(10)2-8/h3-12H,1-2H2/t3-,4+,5+,6- Y
Key: FBPFZTCFMRRESA-GUCUJZIJSA-N Y
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InChI=1/C6H14O6/c7-1-3(9)5(11)6(12)4(10)2-8/h3-12H,1-2H2/t3-,4+,5+,6-
Key: FBPFZTCFMRRESA-GUCUJZIJBM
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SMILES
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O[C@H]([C@@H](O)CO)[C@@H](O)[C@H](O)CO
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| Properties |
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Chemical formula
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C6H14O6 |
| Molar mass |
182.172 g/mol |
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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| N verify (what is YN ?) |
| Infobox references |
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Galactitol (dulcitol) is a sugar alcohol, the reduction product of galactose.[1] In people with galactokinase deficiency, a form of galactosemia, excess dulcitol forms in the lens of the eye leading to cataracts.[2]
Galactitol is produced from galactose in a reaction catalyzed by aldose reductase. Galactose itself comes from the metabolism of the disaccharide lactose into glucose and galactose.
The other common galactose metabolism defect is a defect in galactose-1-phosphate uridylyltransferase, an autosomal recessive disorder, which also causes a buildup of galactitol as a result of increased concentrations of galactose-1-phosphate and galactose. The toxicity associated with galactose-1-phosphate uridylyltransferase deficiency is associated with symptoms of hepatosplenomegaly and mental retardation in addition to the cataracts caused by galactitol buildup.
References
- ^ "Galactitol - Compound Summary". National Center for Biotechnology Information. Retrieved 2008-08-06.
- ^ Roth, KS (September 10, 2007). "Galactokinase Deficiency". eMedicine. WebMD. Retrieved 2008-08-08.
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Fructose and galactose metabolic intermediates
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| Fructose |
- Fructose-1-phosphate → DHAP/Glyceraldehyde → Glyceraldehyde 3-phosphate
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| Galactose |
- Galactose-1-phosphate → Glucose 1-phosphate → Glucose 6-phosphate → Fructose 6-phosphate
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- Uridine diphosphate galactose
- Uridine diphosphate glucose
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| Mannose |
- Mannose-6-phosphate → Fructose 6-phosphate
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Sugar alcohols
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| 1-carbon |
- Methanol[citation needed]
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| 2-carbon |
- Ethylene glycol[citation needed]
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| 3-carbon |
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| 4-carbon |
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| 5-carbon |
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| 6-carbon |
- Mannitol
- Sorbitol
- Galactitol
- Iditol
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| 7-carbon |
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| Deoxy sugar alcohols |
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| Cyclic sugar alcohols |
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| Glycylglycitols |
- Maltitol
- Lactitol
- Isomalt
- Maltotriitol
- Maltotetraitol
- Polyglycitol
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UpToDate Contents
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English Journal
- Enantioselective oxidation of galactitol 1-phosphate by galactitol-1-phosphate 5-dehydrogenase from Escherichia coli.
- Benavente R1, Esteban-Torres M2, Kohring GW3, Cortés-Cabrera Á4, Sánchez-Murcia PA4, Gago F4, Acebrón I1, de Las Rivas B2, Muñoz R2, Mancheño JM1.
- Acta crystallographica. Section D, Biological crystallography.Acta Crystallogr D Biol Crystallogr.2015 Jul 1;71(Pt 7):1540-54. doi: 10.1107/S1399004715009281. Epub 2015 Jun 30.
- Galactitol-1-phosphate 5-dehydrogenase (GPDH) is a polyol dehydrogenase that belongs to the medium-chain dehydrogenase/reductase (MDR) superfamily. It catalyses the Zn(2+)- and NAD(+)-dependent stereoselective dehydrogenation of L-galactitol 1-phosphate to D-tagatose 6-phosphate. Here, three crystal
- PMID 26143925
- Metabolomics reveals that aldose reductase activity due to AKR1B10 is upregulated in hepatitis C virus infection.
- Semmo N1,2, Weber T2, Idle JR1,2, Beyoğlu D2.
- Journal of viral hepatitis.J Viral Hepat.2015 Jul;22(7):617-24. doi: 10.1111/jvh.12376. Epub 2014 Dec 9.
- To understand the changes in the metabolome of hepatitis C virus (HCV)-infected persons, we conducted a metabolomic investigation in both plasma and urine of 30 HCV-positive individuals using plasmas from 30 HCV-negative blood donors and urines from 30 healthy volunteers. Samples were analysed by ga
- PMID 25487531
- Efficient method for the conversion of agricultural waste into sugar alcohols over supported bimetallic catalysts.
- Tathod AP1, Dhepe PL2.
- Bioresource technology.Bioresour Technol.2015 Feb;178:36-44. doi: 10.1016/j.biortech.2014.10.036. Epub 2014 Oct 16.
- Promoter effect of Sn in the PtSn/γ-Al2O3 (AL) and PtSn/C bimetallic catalysts is studied for the conversion of variety of substrates such as, C5 sugars (xylose, arabinose), C6 sugars (glucose, fructose, galactose), hemicelluloses (xylan, arabinogalactan), inulin and agricultural wastes (bagasse, r
- PMID 25453932
Japanese Journal
- Characterization of Mesorhizobium loti L-Rhamnose Isomerase and Its Application to L-Talose Production
- Takata Goro,Uechi Keiko,Taniguchi Eriko [他],KANBARA Yuka,YOSHIHARA Akihide,MORIMOTO Kenji,IZUMORI Ken
- Bioscience, biotechnology, and biochemistry 75(5), 1006-1009, 2011-05-23
- … Application of it in L-talose production from galactitol was achieved by a two-step reaction, indicating that it can be utilized in the large-scale production of L-talose. …
- NAID 10028273062
- Cloning, Expression, and Transcription Analysis of L-Arabinose Isomerase Gene from Mycobacterium smegmatis SMDU
- Takata Goro,Poonperm Wayoon,Rao Devendar [他],SOUDA Akane,NISHIZAKI Tomoe,MORIMOTO Kenji,IZUMORI Ken
- Bioscience, biotechnology, and biochemistry 71(12), 2876-2885, 2007-12-23
- … Transcription analysis using various sugars revealed that this enzyme was significantly induced not only by L-arabinose and D-galactose but also by L-ribose, galactitol, L-ribulose, and L-talitol. …
- NAID 10027521659
- 3D09-3 生物化学的反応を用いた1デオキシ及び6デオキシ-D-タガトースの生産(発酵生理学・発酵工学,一般講演)
- 吉原 明秀,原口 智志,森本 兼司,高田 悟郎,フリート ジョージ,何森 健
- 日本生物工学会大会講演要旨集 平成19年度, 108, 2007-08-02
- NAID 110007323001
Related Links
- The toxicity associated with galactose-1-phosphate uridylyltransferase deficiency is associated with symptoms of hepatosplenomegaly and mental retardation in addition to the cataracts caused by galactitol buildup.
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