For research use only. Not for therapeutic Use.
Levoglucose, also known as L-Glucose, is the L-isomer of glucose. It is the enantiomer of the more common D-glucose. L-Glucose does not occur naturally in higher living organisms, but can be synthesized in the laboratory. L-Glucose is indistinguishable in taste from D-glucose, but cannot be used by living organisms as source of energy because it cannot be phosphorylated by hexokinase, the first enzyme in the glycolysis pathway. Levoglucose may be used as diagnostic aid.
| Catalog Number | R041232 |
| CAS Number | 921-60-8 |
| Synonyms | FM 602; L(-)-Glucose; Levoglucose; l-Glucose; |
| Molecular Formula | C6H12O6 |
| Purity | ≥95% |
| Storage | -20°C |
| IUPAC Name | (2S,3R,4S,5S)-2,3,4,5,6-pentahydroxyhexanal |
| InChI | InChI=1S/C6H12O6/c7-1-3(9)5(11)6(12)4(10)2-8/h1,3-6,8-12H,2H2/t3-,4+,5+,6+/m1/s1 |
| InChIKey | GZCGUPFRVQAUEE-VANKVMQKSA-N |
| SMILES | C(C(C(C(C(C=O)O)O)O)O)O |
| Reference | </br>1:d- Versus l-Glucose Conjugation: Mitochondrial Targeting of a Light-Activated Dual-Mode-of-Action Ruthenium-Based Anticancer Prodrug. Lameijer LN, Hopkins SL, Brevé TG, Askes SH, Bonnet S.Chemistry. 2016 Dec 19;22(51):18484-18491. doi: 10.1002/chem.201603066. Epub 2016 Nov 9. PMID: 27859843 Free PMC Article</br>2:Triacetonide of Glucoheptonic Acid in the Scalable Syntheses of d-Gulose, 6-Deoxy-d-gulose, l-Glucose, 6-Deoxy-l-glucose, and Related Sugars. Liu Z, Yoshihara A, Jenkinson SF, Wormald MR, Estévez RJ, Fleet GW, Izumori K.Org Lett. 2016 Aug 19;18(16):4112-5. doi: 10.1021/acs.orglett.6b02041. Epub 2016 Aug 3. PMID: 27487167 </br>3:Erratum to: Uptake of a fluorescent L-glucose derivative 2-NBDLG into three-dimensionally accumulating insulinoma cells in a phloretin-sensitive manner. Sasaki A, Nagatomo K, Ono K, Yamamoto T, Otsuka Y, Teshima T, Yamada K.Hum Cell. 2016 Jul;29(3):138-139. No abstract available. PMID: 26886928 Free PMC Article</br>4:Imaging hamster model of bile duct cancer in vivo using fluorescent L-glucose derivatives. Yokoyama H, Sasaki A, Yoshizawa T, Kijima H, Hakamada K, Yamada K.Hum Cell. 2016 Jul;29(3):111-21. doi: 10.1007/s13577-015-0131-5. Epub 2016 Feb 3. PMID: 26842558 Free PMC Article</br>5:Uptake of a fluorescent L-glucose derivative 2-NBDLG into three-dimensionally accumulating insulinoma cells in a phloretin-sensitive manner. Sasaki A, Nagatomo K, Ono K, Yamamoto T, Otsuka Y, Teshima T, Yamada K.Hum Cell. 2016 Jan;29(1):37-45. doi: 10.1007/s13577-015-0125-3. Epub 2015 Nov 9. Erratum in: Hum Cell. 2016 Jul;29(3):138-9. PMID: 26553070 Free PMC Article</br>6:Paracoccus laeviglucosivorans sp. nov., an L-glucose-utilizing bacterium isolated from soil. Nakamura A.Int J Syst Evol Microbiol. 2015 Aug 4. doi: 10.1099/ijsem.0.000508. [Epub ahead of print] PMID: 26243274 </br>7:Short and sweet: (D)-glucose to (L)-glucose and (L)-glucuronic acid. Martínez RF, Liu Z, Glawar AF, Yoshihara A, Izumori K, Fleet GW, Jenkinson SF.Angew Chem Int Ed Engl. 2014 Jan 20;53(4):1160-2. doi: 10.1002/anie.201309073. Epub 2013 Dec 5. PMID: 24310928 </br>8:An L-glucose catabolic pathway in Paracoccus species 43P. Shimizu T, Takaya N, Nakamura A.J Biol Chem. 2012 Nov 23;287(48):40448-56. doi: 10.1074/jbc.M112.403055. Epub 2012 Oct 4. PMID: 23038265 Free PMC Article</br>9:Rapid access to 1,6-anhydro-beta-L-hexopyranose derivatives via domino reaction: synthesis of L-allose and L-glucose. D/’Alonzo D, Guaragna A, Napolitano C, Palumbo G.J Org Chem. 2008 Jul 18;73(14):5636-9. doi: 10.1021/jo800775v. Epub 2008 Jun 21. PMID: 18570476 </br>10:Genetically engineered biosynthesis of macrolide derivatives including 4-amino-4,6-dideoxy-L-glucose from Streptomyces venezuelae YJ003-OTBP3. Pageni BB, Oh TJ, Liou K, Yoon YJ, Sohng JK.J Microbiol Biotechnol. 2008 Jan;18(1):88-94. PMID: 18239422 Free Article |
