5441-12-3

Basic information

• Product Name: N-N-BUTYRYL-D-GLUCOSAMINE
• Synonyms: N-N-BUTYRYL-D-GLUCOSAMINE;Butyrylglucosamine;2-Butyrylamino-2-deoxy-D-glucopyranose;N-BUTYRYL-D-GLUCOSAMINE (MIXTURE OF ANOMERS)
• CAS NO: 5441-12-3
• Molecular Formula: C₁₀H₁₉NO₆
• Molecular Weight: 249.26
• Mol File: 5441-12-3.mol
• Article Data: 5

Chemical Properties

• Appearance: /
• CAS DataBase Reference: N-N-BUTYRYL-D-GLUCOSAMINE(CAS DataBase Reference)
• NIST Chemistry Reference: N-N-BUTYRYL-D-GLUCOSAMINE(5441-12-3)
• EPA Substance Registry System: N-N-BUTYRYL-D-GLUCOSAMINE(5441-12-3)

Safety Data

• Hazardous Substances Data: 5441-12-3(Hazardous Substances Data)

Usage

Description

N-N-Butyryl-D-Glucosamine, also known as N-Butyrylglucosamine (GlcNBu), is a chemical compound derived from D-glucosamine, an amino sugar. It is characterized by the attachment of a butyryl group to the nitrogen atom of the glucosamine molecule. This modification enhances its potential applications in various fields, particularly in the biomedical industry.

Uses

Used in Biomedical Applications:
N-N-Butyryl-D-Glucosamine is used as a key compound in the synthesis of N-Butyrylglucosamine (GlcNBu) for biomedical applications. The butyryl modification of glucosamine provides unique properties that can be exploited in the development of new drugs, drug delivery systems, and diagnostic tools.
Used in Pharmaceutical Industry:
In the pharmaceutical industry, N-N-Butyryl-D-Glucosamine is used as an intermediate in the synthesis of various therapeutic agents. Its unique structure allows for the development of drugs with improved pharmacokinetic and pharmacodynamic properties, potentially leading to more effective treatments for a range of diseases.
Used in Drug Delivery Systems:
N-N-Butyryl-D-Glucosamine can be utilized in the design and development of novel drug delivery systems. Its chemical properties make it a suitable candidate for the creation of targeted drug carriers, which can improve the bioavailability and therapeutic efficacy of various drugs.
Used in Diagnostic Tools:
The unique structure of N-N-Butyryl-D-Glucosamine also makes it a valuable component in the development of diagnostic tools. It can be used to create new biomarkers or imaging agents that can help in the early detection and monitoring of diseases.

Upstream product

• 106-31-0 butanoic acid anhydride 
• 1078691-95-8 (+)-D-glucosamine hydrochloride 
• 66-84-2 D-(+)-glucosamine hydrochloride 
• 90-76-6 2-deoxy-2-amino glucose 
• 7165-13-1 acetic butyric anhydride 
• 70741-39-8 2,5-dioxopyrrolidin-1-yl butyrate 

Relevant articles and documents

Highly efficient and selective biocatalytic production of glucosamine from chitin

N-Acetyl glucosamine (GlcNAc) is one of the most abundant biomolecules on Earth and is cheaply available from chitin, a major component of crustaceans. The key step in the conversion of GlcNAc to high-value products is the de-N-acetylation to glucosamine, in itself a valuable dietary supplement that is produced at over 29:000 tons scale per annum by chemical hydrolysis, a process that requires harsh reaction conditions and leads to side products requiring separation. Here, we report for the first time the isolation and characterisation of an enzyme, a deacetylase from Cyclobacterium marinum that is able to catalyse the highly selective quantitative hydrolysis of GlcNAc to glucosamine under mild reaction conditions. This enzyme is small (38 kDa), is easily obtainable by heterologous expression in E. coli, has high turnover rates (kcat=61 s-1), tolerates high substrate concentrations (over 100 g L-1) and can be repeatedly re-used as an immobilised catalyst. When coupled with chitinase, the high selectivity of the enzyme for GlcNAc over other biomolecules allowed one-pot extraction of glucosamine from crude solid mushroom fractions containing chitin, thus allowing for alternative production of glucosamine from non-animal sources, of benefit to consumers with crustacean allergies and vegan diets. We suggest that the deacetylase fills an important gap in the sustainable exploitation of GlcNAc and chitin.

A chemoenzymatic route to N-acetylglucosamine-1-phosphate analogues: Substrate specificity investigations of N-acetylhexosamine 1-kinase

Reports an efficient chemoenzymatic production of an N-acetylhexosamine 1-phophate analogues library by N-acetylhexosamine 1-kinase (NahK) and describes the respective substrate specificity on this enzyme.

Synthesis and antiperoxidant activity of new phenolic O-glycosides

We describe the synthesis of some 3-tert-butyl-4-hydroxyphenyl D-glycopyranosides by reaction of tert-butylhydroquinone with β-D-pentaacetyl-glucose, β-D-pentaacetyl-galactose, 2-acetamido- and 3,4,6-tri-O-acetyl-2-butanamido-2-deoxy-β-D-glucopyranosyl chlorides as well as the formation of anomeric 3-tert-butyl-4-hydroxyphenyl 4,6-di-O-acetyl-2,3-dideoxy-D-erythro-hex-2-eno-pyranosides by reaction between tert-butylhydroquinone and 3,4,6-tri-O-acetyl-D-glucal. All compounds, except 3-tert-butyl-4-hydroxyphenyl α- and β-D-glucopyranosides, inhibited lipid peroxidation with a degree of potency comparable to that of tert-butyl hydroxyanisole.