467448-46-0

Upstream product

• 58479-61-1 tert-butylchlorodiphenylsilane 
• 3459-18-5 4-nitrophenyl N-acetyl-β-D-glucosaminide 

Downstream Products

• 467448-47-1 4-nitrophenyl (2,3,4,6-tetra-O-acetyl-β-D-galactopyranosyl)-(1->4)-2-acetamido-3-O-acetyl-6-O-tert-butyl-diphenylsilyl-2-deoxy-β-D-glucopyranoside 
• 467447-26-3 4-nitrophenyl (2,3,4,6-tetra-O-acetyl-β-D-galactopyranosyl)-(1->4)-2-acetamido-3-O-acetyl-2-deoxy-β-D-glucopyranoside 
• 142925-37-9 4-nitrophenyl β-D-galactopyranosyl-(1->4)-2-acetamido-2-deoxy-β-D-glucopyranoside 

Relevant academic research and scientific papers

N-acetyl-6-sulfo-D-glucosamine as a promising mimic of N-acetyl neuraminic acid

6-Sulfo-D-GlcNAc with a molecular geometry close to that of N-acetylneuraminic acid (Neu5Ac) was hypothesized to serve as a simple Neu5Ac mimic possessing high potential in biochemical and medicinal applications. The hypothesis was evidenced with a neuraminidase inhibition assay using p-nitrophenyl (pNP) 3-, 4-, and 6-sulfo-β-D-GlcNAc (4, 5 and 2a) and 6-sulfo-β-D-Glc 6, in which only pNP 6-sulfo-β-D-GlcNAc 2a was found to show substantial activity.

Synthesis and utility of sulfated chromogenic carbohydrate model substrates for measuring activities of mucin-desulfating enzymes

A chromogenic substrate, 4-nitrophenyl 2-acetamido-2-deoxy-β-D-glucopyranoside 6-sodium sulfate was synthesized and used in combination with β-N-acetylhexosaminidase for detection of the sulfatase, MdsA, by release of 4-nitrophenol. MdsA was originally isolated from the bacterium Prevotella strain RS2 and is believed to be involved in desulfation of sulfomucins, major components of the mucus barrier protecting the human colon surface. The exo nature of the MdsA sulfatase was indicated by its inability to de-esterify the disaccharide 4-nitrophenyl β-D-galactopyranosyl-(1→4)-2-acetamido-2-deoxy-β-D- glucopyranoside 6-sodium sulfate. This latter compound was prepared from monosaccharide precursors by two different methods, the shorter requiring just six steps from 4-nitrophenyl 2-acetamido-2-deoxy-β-D-glucopyranoside and giving an overall yield of 26.4%. The syntheses of 4-nitrophenyl β-D-galactopyranoside 3-triethylammonium sulfate and 6-triethylammonium sulfate and their use in combination with β-galactosidase as chromogenic substrates for detecting Bacteroides fragilis sulfatases with different specificities was also demonstrated.