97055-07-7

Upstream product

• 108-24-7 acetic anhydride 
• 2776-93-4 2-acetamido-1-N-(L-aspart-4-oyl)-2-deoxy-β-D-glucopyranosylamine 
• 77045-60-4 2-amino-2-deoxy-D-glucose hydrazone 

Downstream Products

• 7512-17-6 2-acetamido-2-deoxy-D-glucose 
• 7512-17-6 N-Acetyl-D-glucosamine 

Relevant academic research and scientific papers

AN IMPROVED METHOD FOR THE LIQUID CHROMATOGRAPHY OF THE 1-DEOXY-1-(2-PYRIDYLAMINO)ALDITOL DERIVATIVES OF OLIGOSACCHARIDES AND ITS APPLICATION TO STRUCTURAL STUDIES OF THE CARBOHYDRATE MOIETIES OF GLYCOPROTEINS

The 1-deoxy-1-(2-pyridylamino)alditols prepared by reductive amination of lactose, 2-acetamido-2-deoxy-D-glucose, and 2,5-anhydro-D-mannose have been characterised, and the efficiency of the reductive amination procedure, especially with 2,5-anhydro-D-mannose and 2-amino-2-deoxy-D-glucose hydrazone as starting materials, has been studied.The latter compound, which is a model for the oligosaccharide hydrazones released from glycoproteins and glycopeptides by hydrazinolysis, was first N-acetylated and the hydrazone group was found to be removed hydrolytically when a cation-exchange resin was used for deionisation.Such loss of the hydrazone group is desirable because the N-acetylated hydrazone was not efficiently derivatised by reductive amination.An amine-modified silica column was used to separate the components of a mixture of the pyridylamino derivatives of oligosaccharides from mono- to dodeca-saccharide in 20 min.A neutral fluorescent by-product, formed in all reductive aminations, was identified as (2-amino-1-pyridyl)cyanoborane and was eluted well before monosaccharide derivatives and thus did not interfere with the analysis.

Hydrazinolysis-N-reacetylation of glycopeptides and glycoproteins. Model studies using 2-acetamido-1-N-(L-aspart-4-oyl)-2-deoxy-beta-D-glucopyranosy lamine.

2-Acetamido-1-N-(L-aspart-4-oyl)-2-deoxy-beta-D-glucopyranosyla mine (1) was used as a model glycopeptide to study the hydrazinolysis-N-reacetylation procedure. The major, initial product was the beta-acetohydrazide derivative of 2-acetamido-2-deoxy-D-glucose (2) which gave 2-acetamido-2-deoxy-D-glucose (5) after exposure to acidic conditions. Very mild conditions of hydrolysis of 2 gave a 75-80% overall yield of 5 from 1 after the hydrazinolysis-N-reacetylation procedure. Several other minor compounds were detected which were not converted into 5 upon mild acid hydrolysis, indicating that 20-25% of product cannot be recovered as 5 at the reducing end of oligosaccharides.