6196-57-2

Usage

Uses

Used in Medical Applications:
3-Deoxyhexulose is used as a diagnostic marker for diabetes, helping to identify the presence of the disease in patients' plasma and urine. Its detection aids in the early diagnosis and management of diabetes, enabling timely intervention and treatment.
Used in Research:
3-Deoxyhexulose is utilized in scientific research to study the metabolic pathways and mechanisms associated with diabetes. Understanding its role in the disease can contribute to the development of new therapeutic strategies and interventions for diabetes management.

InChI:InChI=1/C6H12O5/c7-2-4(9)1-5(10)6(11)3-8/h5-8,10-11H,1-3H2/t5-,6+/m0/s1

Upstream product

• 14154-19-9 D-lyxo-3-deoxy-hexose 
• 5517-48-6 3-deoxy-D-arabino-hexose 
• 4134-97-8 3-deoxyglucosone 
• 104048-51-3 (S)-1-((S)-3-Benzyloxymethyl-4,5-dihydro-isoxazol-5-yl)-ethane-1,2-diol 
• 104048-51-3 (R)-1-((S)-3-Benzyloxymethyl-4,5-dihydro-isoxazol-5-yl)-ethane-1,2-diol 
• 104048-40-0 3-Benzyloxymethyl-5-vinyl-4,5-dihydro-isoxazole 
• 6706-59-8 L-Sorbitol 
• 50-99-7 D-glucose 
• 25018-67-1 1,2;4,5-di-O-isopropylidene-β-D-(-)-fructopyranose 
• 334999-08-5 2-(3-benzyloxymethyl-4,5-dihydrooxazol-5-yl)-2-oxoethyl acetate 
• 334999-16-5 (5S)-5-[(1R)-1,2-dihydroxyethyl]-3-benzyloxymethyl-4,5-dihydrooxazole 
• 67104-35-2 3-deoxy-1,2:4,5-di-O-methylethylidene-β-D-ertythro-hex-2-ulopyranose 

Downstream Products

• 1883-75-6 2,5-bis-(hydroxymethyl)furan 
• 3238-40-2 furan-2,5-dicarboxylic acid 

Relevant academic research and scientific papers

Synthesis of Furans from Sugars Via Keto Intermediates

The present invention provides a method of preparing a furan derivative comprising the steps of (a) converting a monosaccharide to provide a keto-intermediate product; and (b) dehydrating the keto-intermediate product to provide a furan derivative; wherein the keto-intermediate product is pre-disposed to forming keto-furanose tautomers in solution. The method may further comprising a step of oxidizing the furan derivative to provide a furandicarboxylic acid or a furandicarboxylic acid derivative.

Permanganate oxidation revisited: Synthesis of 3-deoxy-2-uloses via indium-mediated chain elongation of carbohydrates

Application of the Barbier-type indium-mediated allylation method to suitable substrates offers access to carbohydrates bearing a terminal olefin moiety. The C-C bond, forming reaction generates a defined stereochemistry of the new chiral center and tolerates a wide variety of starting aldehydes thus allowing modifications in the carbohydrate backbone. Further transformations of the alkene moiety via an environmentally benign and subtle controlled protocol using potassium permanganate gives rise to the structural motif of 3-deoxy-2-uloses in good yields. The final part of the reaction sequence focuses on the deprotection of the acetyl groups essential for the success of the oxidation step. The acidic and labile 3-deoxy position of the target molecule is prone to elimination applying standard deacetylation conditions and therefore demands derivatisation of the molecule. The introduction of a thioketal moiety using microwave conditions shows promising results and subsequent standard transformations are applicable leading to the desired products.

Deoxysugars via microbial reduction of 5-acyl-isoxazolines: Application to the synthesis of 3-deoxy-D-fructose and derivatives

5-Acylisoxazolines 3a-d were obtained by 1,3-dipolar cycloaddition from acetoxymethyl vinyl ketone and nitro precursors. Compounds 3a-d were biotransformed by Aspergillus niger into a 1:1 mixture of stereomers of 5-dihydroxyethyl isoxazolines (+)-4a-d (anti) and (-)-5a-d (syn). Both stereomers were obtained in good yields and with high optical purities. Carbonyl reduction by Aspergillus niger produces alcohols of R-configuration thus giving an access to D-sugar analogues: Compound (+)-4d was converted to 3-deoxy-D-erythro-hexulose and several protected derivatives. Total synthesis of 3-deoxy-D-fructose-6-phosphate was also achieved in two steps and 64% overall yield from (+)-4d.

Purification and Characterisation of NADPH-dependent 2-Oxoaldehyde Reductase from Chicken Liver

The enzymes which metabolize 2-oxoaldehyde compounds in a crude extract of chicken liver were examined using 3-deoxyglucosone (3-DG) and methylglyoxal (MG).NADH- and NADPH-dependent reductase activities were observed and the latter was more than the former. NADPH-dependent 2-oxoaldehyde reductase was purified from chicken liver by ammonium sulfate fractionation, and DEAE-cellulose, CM-cellulose, hydroxylapatite, and Sephadex G-100 column chromatographies.The molecular weight of the enzyme was estimated to be 38,000 and 32,000 by SDS-PAGE and gel filtration, respectively.The optimum pH was 6.5-7.0 and this enzyme was stable at pH 7.0-8.0.The Km for 3-DG and MG were 3.75 mM and l.52 mM, respectively.This enzyme had high activities towards 2-oxoaldehyde compounds, such as 3-DG, MG, and phenylglyoxal.This enzyme converted 3-deoxyglucosone (3-DG) to 3-deoxyfructose, and methylgloxal (MG) to acetol.

ENZYMATIC ALDOL REACTION/ISOMERIZATION AS A ROUTE TO UNUSUAL SUGARS

Utilizing fructose diphosphate aldolase and glucose isomerase as catalysts, 3-, 5-, and 6-deoxy- and 6-O-methylhexoses have been synthesized from dihydroxyacetone phosphate or acetol phosphate and the corresponding hydroxypropionaldehydes.

SILYL NITRONATES AND NITRILE OXIDES IN ORGANIC SYNTHESIS. A NOVEL ROUTE TO D,L-DEOXYSUGARS. USE OF ALUMINIUM OXIDE AS SOLID PHASE BASE FOR GENERATION OF NITRILE OXIDES FROM HYDROXIMIC ACID CHLORIDES

Novel methodology is developed for a three step synthesis of deoxyaldoses and deoxyketoses. 1.Regioselective addition of silyl nitronate or nitrile oxide to a diene. 2.Stereospecific hydroxylation of the double bond. 3.Unmasking of the aldol moiety by catalytic reduction of the 2-isoxazoline.The syntheses of D.L-deoxyribose, D,L-oleose, D,L-digitoxose, D,L-2-deoxygalactose, 1,3-dideoxyfructose, 3-deoxyfructose etc. are described.Basic aluminium oxide is introduced as a solid phase base for the one step synthesis of 2-isoxazolines from aldoximes and olefins.An X-ray diffraction study of compound 13c verifies the stereochemical assignments.