18615-50-4

Usage

Uses

Used in Pharmaceutical Industry:
2-ACETAMIDO-2-DEOXY-B-D-GLUCOSYLAMINE is used as a potential active ingredient for developing new drugs and therapies due to its antimicrobial properties and its ability to attract immune cells, which can be beneficial in treating bacterial infections and inflammatory diseases.
Used in Research and Development:
In the field of research, 2-ACETAMIDO-2-DEOXY-B-D-GLUCOSYLAMINE is used as a substrate in enzymatic reactions, facilitating the study of biochemical processes and the development of novel therapeutic agents.
Used in Chemical Synthesis:
2-ACETAMIDO-2-DEOXY-B-D-GLUCOSYLAMINE is used as a building block in the synthesis of complex molecules, contributing to the creation of new compounds with potential applications in various industries, including pharmaceuticals, materials science, and biotechnology.

Upstream product

• 1078691-95-8 (+)-D-glucosamine hydrochloride 
• 1068-57-1 acetic acid hydrazide 
• 6205-72-7 1-N-acetyl-2-acetamido-2-deoxy-β-D-glucopyranosylamine 

Relevant academic research and scientific papers

FURTHER STUDIES OF THE HYDRAZINOLYSIS OF 2-ACETAMIDO-1-N-ACYL-2-DEOXY-β-D-GLUCOPYRANOSYLAMINES

1-Deoxy-D-fructose hydrazone is shown to be the major product of the hydrazinolysis of 2-amino-2-deoxy-D-glucose hydrazone and can be detected as a minor product of the hydrazinolysis of 2-acetamido-1-N-acetyl-2-deoxy-β-D-glucopyranosylamine.The hydrazinolysis conditions (100 deg C, 30 h, no catalyst) of Bayard and Montreuil are inefficient for the cleavage of the amide groups of 2-acetamido-1-N-acetyl-2-deoxy-β-D-glucopyranosylamine, unchanged starting-material and 1-N-acetyl-2-amino-2-deoxy-β-D-glucopyranosylamine accounting for 70percent of the product mixture.Under the same conditions, the hydrazinolysis of 2-acetamido-1-N-(L-β-aspartyl)-2-deoxy-β-D-glucopyranosylamine gave 2-amino-2-deoxy-D-glucose hydrazone as major product together with ca. 14percent of 1-deoxy-D-fructose hydrazone.Participation by the carboxyl group of the asparagine residue is invoked to account for the greater reactivity of the asparagine derivative.The hydrazinium sulphate-catalysed hydrazinolysis gave a higher yield (44percent) of 1-deoxy-D-fructose hydrazone when applied to the asparagine derivative.The implications of these results in relation to the hydrazinolysis of glycopeptides and glycoproteins are discussed.

MODEL STUDIES PERTAINING TO THE HYDRAZINOLYSIS OF GLYCOPEPTIDES AND GLYCOPROTEINS: HYDRAZINOLYSIS OF THE 1-N-ACETYL AND 1-N-(L-β-ASPARTYL) DERIVATIVES OF 2-ACETAMIDO-2-DEOXY-β-D-GLUCOPYRANOSYLAMINE

The products of hydrazinolysis of the 1-N-acetyl and 1-N-(L-β-aspartyl) derivatives of 2-acetamido-2-deoxy-β-D-glucopyranosylamine could not be converted quantitatively into 2-amino-2-deoxy-D-glucose under mild conditions.Proton and (13)C-n.m.r. measurements indicated that the hydrazone of 2-amino-2-deoxy-D-glucose was a major product of the hydrazinolysis of 2-acetamido-1-N-acetyl-2-deoxy-β-D-glucopyranosylamine.Control experiments showed that acetohydrazide is slowly converted into 4-amino-3,5-dimethyl-1,2,4-triazole under the conditions of hydrazinolysis, and hat 2-amino-2-deoxy-D-glucose reacts slowly with acetohydrazide in dilute acetic acid.The implications of these results in relation to the hydrazinolysis of glycopeptides and glycoproteins are discussed.