105265-96-1

Basic information

• Product Name: 2-ACETAMIDO-1,2,5-TRIDEOXY-1,5-IMINO-D-G LUCITOL
• Synonyms: 2-ACETAMIDO-1,2,5-TRIDEOXY-1,5-IMINO-D-G LUCITOL;Acetamide, N-(3S,4R,5R,6R)-4,5-dihydroxy-6-(hydroxymethyl)-3-piperidinyl-;2-acetamido-1,5-imino-1,2,5-trideoxy-D-glucitol;N-[(3S,4R,5R,6R)-4,5-Dihydroxy-6-(hydroxymethyl)piperidin-3-yl]acetamide;N-[(3S,4R,5R,6R)-4,5-Dihydroxy-6-(hydroxyMethyl)-3-piperidinyl]acetaMide;AB05831
• CAS NO: 105265-96-1
• Molecular Formula: C₈H₁₆N₂O₄
• Molecular Weight: 204.22
• Product Categories: Carbohydrates & Derivatives;Glycosidase Inhibitors;Inhibitors
• Mol File: 105265-96-1.mol
• Article Data: 19

Chemical Properties

• Melting Point: 227-228°C
• Boiling Point: 502.5 °C at 760 mmHg
• Flash Point: 257.7 °C
• Appearance: /
• Density: 1.35 g/cm³
• Vapor Pressure: 3.33E-12mmHg at 25°C
• Refractive Index: 1.565
• Storage Temp.: 2-8°C
• CAS DataBase Reference: 2-ACETAMIDO-1,2,5-TRIDEOXY-1,5-IMINO-D-G LUCITOL(CAS DataBase Reference)
• NIST Chemistry Reference: 2-ACETAMIDO-1,2,5-TRIDEOXY-1,5-IMINO-D-G LUCITOL(105265-96-1)
• EPA Substance Registry System: 2-ACETAMIDO-1,2,5-TRIDEOXY-1,5-IMINO-D-G LUCITOL(105265-96-1)

Safety Data

• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 26-36
• WGK Germany: 3
• Hazardous Substances Data: 105265-96-1(Hazardous Substances Data)

Usage

Description

2-ACETAMIDO-1,2,5-TRIDEOXY-1,5-IMINO-D-GLUCITOL, also known as an analogue of deoxynojirimycin, is a white solid with potent inhibitory properties against various N-acetylglucosaminidases. It is a chemical compound derived from the modification of the glucose molecule, which has potential applications in different industries due to its unique chemical properties.

Uses

Used in Pharmaceutical Industry:
2-ACETAMIDO-1,2,5-TRIDEOXY-1,5-IMINO-D-GLUCITOL is used as an inhibitor for N-acetylglucosaminidases, which are enzymes involved in the metabolism of carbohydrates. Its inhibitory action on these enzymes makes it a valuable compound for the development of drugs targeting various diseases and conditions related to carbohydrate metabolism.
Used in Research and Development:
In the field of research and development, 2-ACETAMIDO-1,2,5-TRIDEOXY-1,5-IMINO-D-GLUCITOL serves as a valuable tool for studying the structure, function, and regulation of N-acetylglucosaminidases. This knowledge can be applied to develop new therapeutic strategies and improve our understanding of carbohydrate metabolism and its role in various biological processes.
Used in Chemical Synthesis:
As a chemical compound with unique properties, 2-ACETAMIDO-1,2,5-TRIDEOXY-1,5-IMINO-D-GLUCITOL can be used as a starting material or intermediate in the synthesis of other complex molecules. This can be particularly useful in the development of new drugs, pharmaceuticals, or other chemical products with specific applications.

InChI:InChI=1/C8H16N2O4/c1-4(12)10-5-2-9-6(3-11)8(14)7(5)13/h5-9,11,13-14H,2-3H2,1H3,(H,10,12)/t5-,6+,7+,8+/m0/s1

Upstream product

• 108-24-7 acetic anhydride 
• 121624-33-7 2-Azido-3-O-benzyl-1,2,5-trideoxy-1,5-imino-D-galactitol 
• 114129-23-6 N-benzyl-1,5-dideoxy-1,5-imino-4,6-O-isopropylidene-D-mannitol 
• 121624-25-7 (3aR,5aR,9aR,9bS)-8,8-Dimethyl-2-oxo-hexahydro-1,3,7,9-tetraoxa-2λ⁴-thia-5-aza-cyclopenta[a]naphthalene-5-carboxylic acid benzyl ester 
• 121624-26-8 2-azido-N-benzyloxycarbonyl-1,2,5-trideoxy-1,5-imino-4,6-O-isopropylidene-D-glucitol 
• 121624-31-5 2-Azido-3-O-benzyl-N,6-O-carbonyl-1,2,5-trideoxy-1,5-imino-4-O-methanesulfonyl-D-glucitol 
• 121624-32-6 2-Azido-4-O-benzoyl-3-O-benzyl-N,6-O-carbonyl-1,5-imino-D-galactitol 
• 121624-29-1 2-Azido-3-O-benzyl-N-benzyloxycarbonyl-1,2,5-trideoxy-1,5-imino-D-glucitol 
• 121624-28-0 2-Azido-3-O-benzyl-N-benzyloxycarbonyl-1,2,5-trideoxy-1,5-imino-4,6-O-isopropylidene-D-glucitol 
• 121624-22-4 1,5-dideoxy-1,5-imino-4,6-O-isopropylidene-D-mannitol 
• 121624-24-6 N-benzyloxycarbonyl-1,5-dideoxy-1,5-imino-4,6-O-isopropylidene-D-mannitol 
• 121701-83-5 2-Azido-3-O-benzyl-N,6-O-carbonyl-1,2,5-trideoxy-1,5-imino-D-galactitol 
• 121624-30-4 2-Azido-3-O-benzyl-N,6-O-carbonyl-1,2,5-trideoxy-1,5-imino-D-glucitol 
• 127408-09-7 2-acetamido-N-tert-butoxycarbonyl-1,2,5-trideoxy-1,5-imino-D-galactitol 

Downstream Products

• 114040-97-0 N-((3S,4R,5R,6R)-4,5-dihydroxy-6-(hydroxymethyl)-1-methylpiperidin-3-yl)acetamide 
• 1401914-31-5 1N-methyl-2-acetamido-1,2,5-trideoxy-1,5-imino-D-galactitol 
• 121701-87-9 2-acetamido-1-N-benzyl-1,2,5-trideoxy-1,5-imino-D-galactitol 

Relevant articles and documents

Integrating thin film microfluidics in developing a concise synthesis of DGJNAc: A potent inhibitor of α-N-acetylgalctosaminidases

A simple synthesis, which utilizes a thin film microfluidic reactor for a problematic step, of a potent inhibitor of α-N-acetylhexosaminidases, DGJNAc, has been developed.

Compounds And Methods For The Treatment Of Alzheimer's Disease And/Or Cerebral Amyloid Angiopathy

Described herein are novel compounds and methods for the treatment and/or prevention of cerebral amyloidoses such as Alzheimer's disease (AD) and/or cerebral amyloid angiopathy (CAA).

The development of selective inhibitors of nagz: Increased susceptibility of gram-negative bacteria to β-lactams

The increasing incidence of inducible chromosomal AmpC β-lactamases within the clinic is a growing concern because these enzymes deactivate a broad range of even the most recently developed β-lactam antibiotics. As a result, new strategies are needed to block the action of this antibiotic resistance enzyme. Presented here is a strategy to combat the action of inducible AmpC by inhibiting the β-glucosaminidase NagZ, which is an enzyme involved in regulating the induction of AmpC expression. A divergent route facilitating the rapid synthesis of a series of N-acyl analogues of 2-acetamido-2-deoxynojirimycin is reported here. Among these compounds are potent NagZ inhibitors that are selective against functionally related human enzymes. These compounds reduce minimum inhibitory concentration values for β-lactams against a clinically relevant Gram-negative bacterium bearing inducible chromosomal AmpC β-lactamase, Pseudomonas aeruginosa. The structure of a NagZ-inhibitor complex provides insight into the molecular basis for inhibition by these compounds. The development of selective and potent inhibitors of the β-glucosaminidase NagZ, which is an important enzyme in AmpC β-lactamase expression, based on the inhibitor 2-acetamido-2-deoxynojirimycin is described. In addition, the structure of a NagZ-inhibitor complex provides insight into the molecular basis for inhibition by these compounds.