16867-64-4

Basic information

• Product Name: 2-deoxy-D-lyxo-hexonic acid
• Synonyms: 2-Deoxy-D-lyxo-hexonic acid; D-lyxo-hexonic acid, 2-deoxy-
• CAS NO: 16867-64-4
• Molecular Formula: C₆H₁₂O₆
• Molecular Weight: 180.1559
• Mol File: 16867-64-4.mol
• Article Data: 3

Chemical Properties

• Boiling Point: 556.8°C at 760 mmHg
• Flash Point: 304.6°C
• Density: 1.589g/cm³
• Vapor Pressure: 1.03E-14mmHg at 25°C
• Refractive Index: 1.574
• CAS DataBase Reference: 2-deoxy-D-lyxo-hexonic acid(CAS DataBase Reference)
• NIST Chemistry Reference: 2-deoxy-D-lyxo-hexonic acid(16867-64-4)
• EPA Substance Registry System: 2-deoxy-D-lyxo-hexonic acid(16867-64-4)

Safety Data

• Hazardous Substances Data: 16867-64-4(Hazardous Substances Data)

Upstream product

• 61-58-5 2-deoxy-D-arabino-hexopyranose 
• 154-17-6 D-2-deoxyglucose 

Downstream Products

• 61244-22-2 N-phenyl-2-deoxy-D-gluconohydrazide 
• 42400-32-8 2-deoxy-D-arabino-hexono-1,4-lactone 
• 488-82-4 D-Arabitol 

Relevant articles and documents

Rare keto-aldoses from enzymatic oxidation: Substrates and oxidation products of pyranose 2-oxidase

Pyranose oxidases are known to oxidise D-glucose, D-xylose and L- sorbose to keto-aldoses, biochemically interesting compounds that may also be used for synthetic purposes in a variety of reactions. In this study pyranose oxidase from the basidiomycete Peniophora gigantea was investigated, and it was found that this enzyme is able to oxidise a broad variety of substrates very effectively. In analogy to its natural mode of action, most substrates are oxidised regioselectively in position 2. Certain compounds, however, are converted into 3-keto derivatives, and the enzyme even exhibits transfer potential, that is, disscharides are formed from β-glycosides of higher alcohols. Substrates that may be oxidised at C-2 in yields between 40-98% are D-allose, D-galactose, 6-deoxy-D-glucose, D-gentiobiose, α-D-glucopyranosyl fluoride and the very interesting 3-deoxy-D-glucose. 1,5-Anhydro-D-glucitol (1-deoxy-D-glucose) is very effectively oxidised in position 2 in 98% yield and additionally gives a product of dioxidation at C-2 and C-3 upon prolonged reaction time Selective oxidation at C-3 was found for 2-deoxy-D-glucose in very good yields and for methyl β-D-gluco- and methyl β-galactopyranoside in lower yields. All oxidation products were unequivocally characterised by NMR spectroscopy and/or chemical derivatisation. In addition, the kinetic data of the enzymatic reactions were determined for all substrates. On the basis of these data and the structural characteristics of the substrates, a model for the minimal structural requirements of the enzyme-substrate interaction is suggested. The enzyme presumably uses two different binding modes for the regioselective C-2 and the C-3 oxidations, which are described.

Oxidation of 2-deoxy-D-arabino-hexose ("2-deoxy-D-glucose") by alkaline hydrogen peroxide

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