2-Keto-D-Glucose

• CAT Number: R000724
• CAS Number: 1854-25-7
• Molecular Formula: C6H10O6
• Molecular Weight: 178.14
• Purity: ≥95%
• Synonyms: (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
• InChIKey: DCNMIDLYWOTSGK-HSUXUTPPSA-N
• SMILES: C(C(C(C(C(=O)C=O)O)O)O)O

2-Keto-D-Glucose (D-Glucosone) is a key intermediate in a secondary metabolic pathway leading to the antibiotic Cortalcerone. 2-Keto-D-Glucose is also an intermediate in the conversion of D-glucose into D-fructose. 2-Keto-D-Glucose is found in various natural sources, including fungi, algae, and shellfish[1][2].
Pyrroloquinoline quinone-dependent 2-keto-D-glucose (2KG) dehydrogenase (2KGDH) has high specificity for the oxidation of 2-Keto-D-Glucose to 2-keto-D-gluconic acid (2KGA). P. aureofaciens (Pa2KGDH) specifically preferred 2KG as a substrate and oxidized the C-1 position of 2KG, indicating that the enzyme is a 2KGDH[3].

Reference

[1]. Sun, Lianhong, et al. Engineering galactose oxidase to increase expression level in E. coli, enhance thermostability, and introduce novel activities. Dissertation (Ph.D.), California Institute of Technology.

[2]. zawa K, et al. A novel pyrroloquinoline quinone-dependent 2-keto-D-glucose dehydrogenase from Pseudomonas aureofaciens. J Bacteriol. 2015 Apr;197(8):1322-9.
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[3]. Te-ning E.Liu, et al. Convenient, laboratory procedure for producing solid d-arabino-hexos-2-ulose (d-glucosone). Carbohydrate Research. Volume 113, Issue 1, 16 February 1983, Pages 151-157.