| SKU | Size | Availability | Price | Qty |
|---|---|---|---|---|
| K465240-100mg | 100mg | Available within 8-12 weeks(?) Production requires sourcing of materials. We appreciate your patience and understanding. | $675.90 |
| Synonyms | D-Arabino-2-hexosulose | D-Arabino-hexos-2-ulose | D-glucosone | Galactosone | PD053744 | Arabino-hexosulose | NSC 120040 | Q27123425 | SCHEMBL818364 | W-201665 | (3S,4R,5R)-3,4,5,6-tetrahydroxy-2-oxohexanal | aldehydo-2-keto-D-glucose | D-arabino-hexosul |
|---|---|
| Specifications & Purity | ≥98%(TLC) |
| Product Description | Description 2-Keto-D-glucose (D-Glucosone) is a key intermediate of a secondary metabolic pathway leading to the antibiotic cortalcerone. D-Glucosone is a substrate that may be used to identify, differentiate and characterize hexokinase(s). |
| IUPAC Name | (3S,4R,5R)-3,4,5,6-tetrahydroxy-2-oxohexanal |
|---|---|
| INCHI | InChI=1S/C6H10O6/c7-1-3(9)5(11)6(12)4(10)2-8/h1,4-6,8,10-12H,2H2/t4-,5-,6-/m1/s1 |
| InChi Key | DCNMIDLYWOTSGK-HSUXUTPPSA-N |
| Canonical SMILES | C(C(C(C(C(=O)C=O)O)O)O)O |
| Isomeric SMILES | C([C@H]([C@H]([C@@H](C(=O)C=O)O)O)O)O |
| WGK Germany | 3 |
| PubChem CID | 159630 |
| Molecular Weight | 178.14 |
| Beilstein | 1725425 |
Enter Lot Number to search for COA:
| Refractive Index | n20D1.55 (Predicted) |
|---|---|
| Boil Point(°C) | 480.99° C at 760 mmHg (Predicted) |
| Melt Point(°C) | 124.69° C (Predicted) |
| WGK Germany | 3 |
|---|---|
| RIDADR | NONHforallmodesoftransport |
| 1. J R Baker,D V Zyzak,S R Thorpe,J W Baynes. (1994-10-01) Chemistry of the fructosamine assay: D-glucosone is the product of oxidation of Amadori compounds.. Clinical chemistry, 40 ((10)): (1950-1955). [PMID:7923778] |
| 2. K Kobayashi,K Yoshimoto,K Hirauchi,K Uchida. (1994-03-01) Determination of glycated proteins in biological samples based on colorimetry of 2-keto-glucose released with hydrazine.. Biological & pharmaceutical bulletin, 17 ((3)): (365-369). [PMID:8019498] |
| 3. K J Wells-Knecht,D V Zyzak,J E Litchfield,S R Thorpe,J W Baynes. (1995-03-21) Mechanism of autoxidative glycosylation: identification of glyoxal and arabinose as intermediates in the autoxidative modification of proteins by glucose.. Biochemistry, 34 ((11)): (3702-3709). [PMID:7893666] |
| 4. F Giffhorn. (2001-01-11) Fungal pyranose oxidases: occurrence, properties and biotechnical applications in carbohydrate chemistry.. Applied microbiology and biotechnology, 54 ((6)): (727-740). [PMID:11152063] |
| 5. G Treitz,G Maria,F Giffhorn,E Heinzle. (2001-02-15) Kinetic model discrimination via step-by-step experimental and computational procedure in the enzymatic oxidation of D-glucose.. Journal of biotechnology, 85 ((3)): (271-287). [PMID:11173094] |
| 6. Torbjörn Linden,Arieh Cohen,Reinhold Deppisch,Per Kjellstrand,Anders Wieslander. (2002-07-12) 3,4-Dideoxyglucosone-3-ene (3,4-DGE): a cytotoxic glucose degradation product in fluids for peritoneal dialysis.. Kidney international, 62 ((2)): (697-703). [PMID:12110035] |
| 7. Ryoji Nagai,Yuka Unno,Miki Cristina Hayashi,Shuichi Masuda,Fumitaka Hayase,Naohide Kinae,Seikoh Horiuchi. (2002-08-28) Peroxynitrite induces formation of N( epsilon )-(carboxymethyl) lysine by the cleavage of Amadori product and generation of glucosone and glyoxal from glucose: novel pathways for protein modification by peroxynitrite.. Diabetes, 51 ((9)): (2833-2839). [PMID:12196478] |
| 8. Stefan Freimund,Sabine Köpper. (2003-12-31) The composition of 2-keto aldoses in organic solvents as determined by NMR spectroscopy.. Carbohydrate research, 339 ((2)): (217-220). [PMID:14698879] |
| 9. Teruyuki Usui,Miku Yoshino,Hirohito Watanabe,Fumitaka Hayase. (2007-09-11) Determination of glyceraldehyde formed in glucose degradation and glycation.. Bioscience, biotechnology, and biochemistry, 71 ((9)): (2162-2168). [PMID:17827699] |
| 10. Teruyuki Usui,Satoshi Yanagisawa,Mio Ohguchi,Miku Yoshino,Risa Kawabata,Junko Kishimoto,Yumi Arai,Kaoru Aida,Hirohito Watanabe,Fumitaka Hayase. (2007-10-12) Identification and determination of alpha-dicarbonyl compounds formed in the degradation of sugars.. Bioscience, biotechnology, and biochemistry, 71 ((10)): (2465-2472). [PMID:17928698] |
| 11. Amin Karmali,José Coelho. (2010-09-28) Bioconversion of D-glucose into D-glucosone by glucose 2-oxidase from Coriolus versicolor at moderate pressures.. Applied biochemistry and biotechnology, 163 ((7)): (906-917). [PMID:20872184] |
| 12. Stefan Mittelmaier,Michael Fünfrocken,Dominik Fenn,Robert Berlich,Monika Pischetsrieder. (2011-07-05) Quantification of the six major α-dicarbonyl contaminants in peritoneal dialysis fluids by UHPLC/DAD/MSMS.. Analytical and bioanalytical chemistry, 401 ((4)): (1183-1193). [PMID:21725830] |
| 13. Sabrina Gensberger,Stefan Mittelmaier,Marcus A Glomb,Monika Pischetsrieder. (2012-03-03) Identification and quantification of six major α-dicarbonyl process contaminants in high-fructose corn syrup.. Analytical and bioanalytical chemistry, 403 ((10)): (2923-2931). [PMID:22382856] |
| 14. Hiram F Ramírez-Cahero,Ma Angeles Valdivia-López. (2017-12-31) Effect of gamma radiation on sugars and vitamin C: Radiolytic pathways.. Food chemistry, 245 (1131-1140). [PMID:29287332] |
| 15. Peter L Herzog,Leander Sützl,Beate Eisenhut,Daniel Maresch,Dietmar Haltrich,Christian Obinger,Clemens K Peterbauer. (2019-04-28) Versatile Oxidase and Dehydrogenase Activities of Bacterial Pyranose 2-Oxidase Facilitate Redox Cycling with Manganese Peroxidase In Vitro.. Applied and environmental microbiology, 85 ((13)): [PMID:31028028] |
| 16. Xue Zhao,Yuliya Hrynets,Mirko Betti. (2019-10-14) Cold non-enzymatic browning of glucosamine in the presence of metmyoglobin induces glucosone and deoxymyoglobin formation.. Food chemistry, 305 (125504-125504). [PMID:31606691] |
| 17. A Araki. (1998-02-12) [Oxidative stress and diabetes mellitus: a possible role of alpha-dicarbonyl compounds in free radical formation].. Nihon Ronen Igakkai zasshi. Japanese journal of geriatrics, 34 ((9)): (716-720). [PMID:9430981] |
| 18. B Nidetzky,M Klimacek,P Mayr. (2001-08-22) Transient-state and steady-state kinetic studies of the mechanism of NADH-dependent aldehyde reduction catalyzed by xylose reductase from the yeast Candida tenuis.. Biochemistry, 40 ((34)): (10371-10381). [PMID:11513616] |
| 19. Stefan Freimund,Lars Baldes,Alexander Huwig,Friedrich Giffhorn. (2002-09-28) Enzymatic synthesis of D-glucosone 6-phosphate (D-arabino-hexos-2-ulose 6-(dihydrogen phosphate)) and NMR analysis of its isomeric forms.. Carbohydrate research, 337 ((17)): (1585-1587). [PMID:12350328] |
| 20. Yoshimitsu Takakura,Shigeru Kuwata. (2004-01-20) Purification, characterization, and molecular cloning of a pyranose oxidase from the fruit body of the basidiomycete, Tricholoma matsutake.. Bioscience, biotechnology, and biochemistry, 67 ((12)): (2598-2607). [PMID:14730138] |
| 21. Nobuyuki Yoshida,Shin-ichi Akazawa,Ayako Kuwahara,Tohoru Katsuragi,Yoshiki Tani. (2005-06-24) Fructosyl-amino acid oxidases of Aspergillus oryzae are induced by the reaction product, glucosone.. FEMS microbiology letters, 248 ((2)): (141-145). [PMID:15972252] |
| 22. Vincent M Monnier,David R Sell,Zhenyu Dai,Ina Nemet,Francois Collard,Jianye Zhang. (2008-05-02) The role of the amadori product in the complications of diabetes.. Annals of the New York Academy of Sciences, 1126 (81-88). [PMID:18448799] |
| 23. Kunchala Rungsrisuriyachai,Giovanni Gadda. (2009-01-17) A pH switch affects the steady-state kinetic mechanism of pyranose 2-oxidase from Trametes ochracea.. Archives of biochemistry and biophysics, 483 ((1)): (10-15). [PMID:19146821] |
| 24. Jenny Gobert,Marcus A Glomb. (2009-08-29) Degradation of glucose: reinvestigation of reactive alpha-Dicarbonyl compounds.. Journal of agricultural and food chemistry, 57 ((18)): (8591-8597). [PMID:19711949] |
| 25. Stefan Mittelmaier,Michael Fünfrocken,Dominik Fenn,Thomas Fichert,Monika Pischetsrieder. (2010-03-02) Identification and quantification of the glucose degradation product glucosone in peritoneal dialysis fluids by HPLC/DAD/MSMS.. Journal of chromatography. B, Analytical technologies in the biomedical and life sciences, 878 ((11-12)): (877-882). [PMID:20189892] |
| 26. Xiu-Min Chen,David D Kitts. (2011-06-01) Correlating changes that occur in chemical properties with the generation of antioxidant capacity in different sugar-amino acid Maillard reaction models.. Journal of food science, 76 ((6)): (C831-C837). [PMID:21623789] |
| 27. Wenhui Zhang,Anthony S Serianni. (2012-06-02) Phosphate-catalyzed degradation of D-glucosone in aqueous solution is accompanied by C1-C2 transposition.. Journal of the American Chemical Society, 134 ((28)): (11511-11524). [PMID:22650268] |
| 28. Anikó Várnai,Kiwamu Umezawa,Makoto Yoshida,Vincent G H Eijsink. (2018-04-01) The pyrroloquinoline-quinone dependent pyranose dehydrogenase from Coprinopsis cinerea (CcPDH) drives lytic polysaccharide monooxygenase (LPMO) action.. Applied and environmental microbiology, [PMID:29602785] |
