78963-40-3

Basic information

• Product Name: 2L-(2,4/3,5)-2,3,4,5-tetrahydroxycyclohexan-1-one
• Synonyms: 2L-(2,4/3,5)-2,3,4,5-tetrahydroxycyclohexan-1-one
• CAS NO: 78963-40-3
• Molecular Weight: 162.142
• Mol File: 78963-40-3.mol
• Article Data: 7

Chemical Properties

• CAS DataBase Reference: 2L-(2,4/3,5)-2,3,4,5-tetrahydroxycyclohexan-1-one(CAS DataBase Reference)
• NIST Chemistry Reference: 2L-(2,4/3,5)-2,3,4,5-tetrahydroxycyclohexan-1-one(78963-40-3)
• EPA Substance Registry System: 2L-(2,4/3,5)-2,3,4,5-tetrahydroxycyclohexan-1-one(78963-40-3)

Safety Data

• Hazardous Substances Data: 78963-40-3(Hazardous Substances Data)

Upstream product

• 2280-44-6 D-Glucose 
• 1356858-93-9 C₁₈H₁₅NO₇ 
• 128387-20-2 L-1,2-O-isopropylidene-myo-inositol 
• 488-76-6 (-)-viburnitol 
• 177471-67-9 3,4,5,6-tetra-O-benzyl-2-deoxy-scyllo-inosose 
• 87-89-8 D-myo-inositol 

Downstream Products

• 693245-36-2 (3S,4S,5R,6S,7R)-4,5,6,7-tetrahydroxy-1-oxaspiro[2,5]octane 
• 177898-42-9 (1R,2S,3S,4R)-5-hydroxymethyl-1-octylamino-2,3,4-trihydroxycyclohex-5-ene 
• 102490-44-8 Acetic acid (1R,2S,6R)-2,6-diacetoxy-5-methylene-cyclohex-3-enyl ester 
• 942065-91-0 C₁₅H₁₉BrO₈ 
• 1350889-90-5 C₁₂H₁₄O₇ 
• 613-03-6 1,2,4-triacetoxybenzene 
• 1133953-73-7 Galβ1->4DOI 
• 869496-55-9 1L-(1,3/2,4)-5-methylene-1,2,3,4-cyclohexanetetrol tetra-acetate 
• 115304-41-1 1L-(1,2,4/3,5)-1-C-(hydroxymethyl)-1,2,3,4,5-cyclohexanepentol 
• 533-73-3 1,2,4-Trihydroxybenzene 
• 75419-36-2 3-amino-2,3-dideoxy-D-myo-inositol 
• 24924-09-2 1,2,3,5-tetraacetoxy-benzene 
• 16276-07-6 1,2,3,4-tetraacetoxy-benzene 
• 1190844-34-8 (4S,5R,6S)-4,5,6-trihydroxy-2-cyclohexene-1-one 

Relevant articles and documents

Molecular cloning of the gene for the key carbocycle-forming enzyme in the biosynthesis of 2-deoxystreptamine-containing aminocyclitol antibiotics and its comparison with dehydroquinate synthase

The 2-deoxystreptamine aglycon is a common structural feature found in aminocyclitol antibiotics including neomycin, kanamycin, tobramycin, gentamicin, sisomicin, butirosin and ribostamycin. A key enzyme involved in the biosynthesis of the 2-deoxystreptamine moiety is 2-deoxy-scyllo-inosose (DOI) synthase which catalyses the carbocycle formation from D-glucose-6-phosphate to 2-deoxy-scyllo-inosose. The recent success of isolating the 2-deoxy-scyllo-inosose synthase from Bacillus circulans prompted us to clone the gene responsible for this important enzyme by the use of reverse genetics approach. With the aid of DNA probes constructed on the basis of the amino-terminal sequence of the purified 42 kDa subunit of the enzyme, the responsible gene btrC was successfully cloned. Subsequently the btrC gene was heterologously expressed in Escherichia coli, and the 2-deoxy-scyllo-inosose synthase activity of the recombinant polypeptide was confirmed by chemical analysis. The btrC gene encodes a protein composed of 368 amino acids with a molecular mass of 40.7 kDa. Our previous proposal for the similarity of 2-deoxy-scyllo-inosose synthase to dehydroquinate synthase has been confirmed on the basis of their amino acid sequences. Significant differences in the sequences can also be observed however, particularly in the crucial substrate recognition regions. Comparison of the BtrC sequence with those of biosynthetic enzymes for other related microbial products is also discussed.

Gene expression cassette and a transformant, and a method for manufacturing 2-deoxy-scyllo-inosose and a method for purifying 2-deoxy-scyllo-inosose using said transformant

A transformant is prepared to insert at least a gene expression cassette comprising a gene involved in the synthesis of 2-deoxy-scyllo-inosose into E. coli as host cells. A 2-deoxy-scyllo-inosose is synthesized from D-glucose, oligosaccharide, polysaccharide, starch and rice bran, using the transformant. A culture solution containing the 2-deoxy-scyllo-inosose is treated with a mixed bed or double bed type column comprising a hydrogen form of strong acidic cation exchange resin and an organic ion form of basic anion exchange resin. The 2-deoxy-scyllo-inosose as purified is reacted with trimethoxymethane to convert into 2-deoxy-scyllo-inosose dimethylketal, and the dimethylketal is crystallized and purified. Then, DOI is highly purified through hydrolyzing the dimethylketal in the presence of acid.

Convenient synthesis of (+)-valiolamine and (-)-1-epi-valiolamine from (-)-vibo-quercitol

The synthesis of (+)-valiolamine and (-)-1-epi-valiolamine using bioconversion of (-)-vibo-quercitol was investigated. The quercitols were separated and purified by combination of chromatography on ion-exchange-resin columns and recrystallization. Valiolamine was isolated from fermentation broth of antibiotic validamycins. The obtained crude ketone was subjected to C-C bond formation conditions in which diazomethane was considered adequate in polar and protic solvsnts.