14307-03-0

Basic information

• Product Name: 2-amino-2-deoxyglucitol
• Synonyms: 2-amino-2-deoxyglucitol;2-Amino-2-deoxy-D-glucitol;D-Glucosaminitol;D-Glucosaminol
• CAS NO: 14307-03-0
• Molecular Formula: C₆H₁₅NO₅
• Molecular Weight: 0
• Mol File: 14307-03-0.mol
• Article Data: 6

Chemical Properties

• Boiling Point: 530.7°Cat760mmHg
• Flash Point: 274.7°C
• Appearance: /
• Density: 1.506g/cm³
• Vapor Pressure: 1.78E-13mmHg at 25°C
• Refractive Index: 1.595
• CAS DataBase Reference: 2-amino-2-deoxyglucitol(CAS DataBase Reference)
• NIST Chemistry Reference: 2-amino-2-deoxyglucitol(14307-03-0)
• EPA Substance Registry System: 2-amino-2-deoxyglucitol(14307-03-0)

Safety Data

• Hazardous Substances Data: 14307-03-0(Hazardous Substances Data)

Usage

Aliases

2-deoxyglucitol, 2DG

Structure

Similar to glucose

Source

Derived from glucose

Function

Regulates blood sugar levels

Biomarker for Diabetes

Studied for its potential use as a biomarker for diabetes

Glycemic Control

Levels in blood linked to individuals' glycemic control

Therapeutic Potential

Investigated for potential therapeutic effects in managing diabetes and its complications

Antioxidant Properties

Shown to have antioxidant properties

Role in Oxidative Stress

May have a role in protecting against oxidative stress-related conditions

InChI:InChI=1/C6H15NO5/c7-3(1-8)5(11)6(12)4(10)2-9/h3-6,8-12H,1-2,7H2/t3-,4+,5+,6+/m0/s1

Upstream product

• 66-84-2 D-(+)-glucosamine hydrochloride 
• 4271-28-7 2-acetylamino-2-deoxy-D-glucitol 
• 83050-21-9 1,3-di-O-benzyl-2-benzylamino-4,6-O-benzylidene-2-deoxy-D-glucitol 
• 29886-32-6 β-D-GlcpNAc(1->4)-D-GlcNAc-ol 
• 90-76-6 2-deoxy-2-amino glucose 
• 3416-24-8 2-amino-2-deoxyglucose 
• 7732-18-5 water 
• 7512-17-6 N-Acetyl-D-glucosamine 
• 4229-38-3 2-acetamido-2-deoxy-β-D-glucopyranosylamine 
• 16405-05-3 2-acetamido-1-N-(1-benzyloxy-N-benzyloxycarbonyl-4-L-aspartyl)-2-deoxy-β-D-glucopyranosylamine 
• 102039-77-0 N,N'-diacetylchitobiosamine 

Downstream Products

• 56211-19-9 2-acetamido-2-deoxy-D-glucitol pentaacetate 
• 5513-52-0 2-(N-carbobenzyloxyglycylamino)-2-deoxy-D-glucitol 
• 223681-55-8 2,2-Dimethyl-propionic acid (2S,3R,4S,5R)-2-benzyloxycarbonylamino-6-(2,2-dimethyl-propionyloxy)-3,4,5-trihydroxy-hexyl ester 
• 154-17-6 D-2-deoxyglucose 
• 119897-59-5 ((1S,2R,3S,4R)-2,3,4,5-Tetrahydroxy-1-hydroxymethyl-pentyl)-carbamic acid benzyl ester 
• 14278-76-3 2-(2,4-dinitro-anilino)-2-deoxy-D-glucitol 

Relevant articles and documents

Purification and characterization of D-glucosaminitol dehydrogenase from Agrobacterium radiobacter.

D-Glucosaminitol dehydrogenase, which catalyzes the conversion of D-glucosaminitol to 3-keto-D-glucosaminitol, was purified to apparent homogeneity from extracts of Agrobacterium radiobacter. This organism has constitutively depressed levels of the enzyme but expression of the enzyme is induced by addition of D-glucosamine to the medium. Purification included ammonium sulfate fractionation and chromatography on columns of DEAE-Sephacel, Octyl-Sepharose CL-4B, and Cellulofine. The purified enzyme migrated as a single band, coinciding with dehydrogenase activities specific for D-glucosaminitol and ethanol, when electrophoresed on a 7.5% polyacrylamide gel at pH 8.0. Electrophoresis on a 12.5% PAGE in the presence of 1% SDS also yielded a single band. The enzyme had an apparent molecular mass of 79 kDa, as measured by the pattern of elution from a column of Cellulofine. The results indicated that the enzyme was a dimer of identical (or nearly identical) subunits of 39.5 kDa. D-Glucosaminitol dehydrogenase required NAD+ as a cofactor and used ethanol as the preferred substrate, as well as aliphatic alcohols with 2 to 4 carbon atoms, D-glucosaminitol, D-glucosaminate, DL-allothreonine, glycerol, and erythritol as additional substrates. In 50 mM Tris-HCl buffer (pH 9.0) at 25 degrees C, the K(m) for D-glucosaminitol, ethanol, and NAD+ were 2.2, 2.0, and 0.08 mM, respectively. The enzyme had a pH optimum of 10 for D-glucosaminitol and 8.5 for ethanol. The enzyme lost substantial activity when treated with pyrazole, with certain reagents that react with sulfhydryl groups and with Zn2+ ion. The various results together suggest that the enzyme exploits different amino acid residues for the dehydrogenation of ethanol and of D-glucosaminitol.

Isolation of 2-Amino-2-deoxy-D-mannitol from Culture Broth of Streptomyces species

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NEW SIMPLE SYNTHESIS OF 2-ACETAMIDO-2-DEOXY-β-D-GLUCOPYRANOSYLAMINE AND 2-ACETAMIDO-4-O-(2-ACETAMIDO-2-DEOXY-β-D-GLUCOPYRANOSYL)-2-DEOXY-β-D-GLUCOPYRANOSYLAMINE AND PREPARATION OF THEIR N-ACYL DERIVATIVES

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