26112-88-9

Usage

InChI:InChI=1/C17H22N2O11/c1-8(21)18-13-11(22)6-17(16(25)26,30-15(13)14(24)12(23)7-20)29-10-4-2-9(3-5-10)19(27)28/h2-5,11-15,20,22-24H,6-7H2,1H3,(H,18,21)(H,25,26)

Upstream product

• 100-02-7 4-nitro-phenol 
• 6770-41-8 Methyl (5-acetamido-4,7,8,9-tetra-O-acetyl-3,5-dideoxy-β-D-glycero-D-galacto-2-nonulopyranosyl chloride)onate 
• 67670-69-3 N-acetyl-4,7,8,9-tetra-O-acetyl-2-chloro-2-deoxyneuraminic acid methyl ester 
• 294183-03-2 methyl (p-nitrophenyl 5-acetamido-4,7,8,9-tetra-O-acetyl-5-deoxy-3-O-(phenoxythiocarbonyl)-α-D-erythro-L-gluco-2-nonulopyranosid)onate 
• 251941-09-0 methyl (p-nitrophenyl 5-acetamido-4,7,8,9-tetra-O-acetyl-5-deoxy-α-D-erythro-L-gluco-2-nonulopyranosid)onate 
• 824-78-2 4-nitrophenol sodium salt 
• 109681-08-5 methyl 5-acetamido-4,7,8,9-tetra-O-acetyl-2-bromo-2,5-dideoxy-D-erythro-α-L-gluco-non-2-ulopyranosonate 
• 59694-35-8 methyl <(4-nitrophenyl) 5-acetamido-3,5-dideoxy-α-D-glycero-D-galacto-2-nonulopyranosid>onate 
• 59694-37-0 methyl (4-nitrophenyl 5-acetamido-4,7,8,9-tetra-O-acetyl-3,5-dideoxy-2-oxy-α-D-glycero-D-galacto-2-nonulopyranosid)onate 

Downstream Products

• 100-02-7 4-nitro-phenol 
• 489-46-3 sialic acid 
• 1000890-54-9 methyl (5-acetamido-3,5-dideoxy-α-D-glycero-D-galacto-2-nonulopyranosylonic acid)-(2->3)-(β-D-galactopyranosyl)-(1->6)-α-D-glucopyranoside 
• 1000890-32-3 4-nitrophenyl (5-acetamido-9-O-butanoyl-3,5-dideoxy-α-D-glycero-D-galacto-2-nonulopyranosidonic acid) 
• 24967-27-9 2,3-dehydro-2-deoxy-N-acetylneuraminic acid 

Relevant academic research and scientific papers

Syntheses of C-3-modified sialylglycosides as selective inhibitors of influenza hemagglutinin and neuraminidase

In an effort to develop new structures as inhibitors of both influenza virus proteins hemagglutinin and neuraminidase, a series of sialic acid derivatives, including those with one of the hydrogen atoms at the C-3 position replaced by either OH or F, were synthesized. The sialic acid derivative with a 3-eq-OH group was first synthesized by means of a new process and used as the key intermediate for further derivatization at the C- 3 position. The stability of these compounds under acid- and sialidase- catalyzed hydrolysis conditions was studied, and the results showed that these compounds exhibit stronger resistance towards both conditions than their parent p-nitrophenyl α-sialoside. Further inhibition assay indicated that the 3-ax-OH or F derivatives 4, 5, and 24, the 4-epimer of 4, are effective specific inhibitors of the sialidases from Clostridium perfringens, among other bacterial sialidases tested. The 3-eq-OH derivative 3, however, showed little inhibition. The same tendency was observed for the inhibition of human influenza sialidases N1 and N2. Compounds 3-5 and sialic acid were then converted into the distealoylphosphatidylethanolamine conjugates. Of these liposome-like compounds, the ones from 4 and 5 showed potent and selective inhibitory activities against the hemagglutinin H3 subtype, but displayed resistance to the influenza virus neuraminidases N1 and N2.

PHASE-TRANSFER-CATALYZED SYNTHESIS OF ARYL α-KETOSIDES OF N-ACETYLNEURAMINIC ACID. A 2-METHYLFLUORAN-6-YL GLYCOSIDE OF N-ACETYLNEURAMINIC ACID, 2-METHYL-6-(5-ACETAMIDO-3,5-DIDEOXY-α-D-glycero-D-galacto-NONULOPYRANOSYLONIC ACID)XANTHENE-9-SPIRO-1'-ISOBENZOFURAN-3'-ONE, A NEW SUBSTRATE..

Glycosidation of N-acetylneuraminic acid by phase-transfer catalysis in chloroform-aqueous alkali gave several known and some new aryl α-ketosides in a short reaction time and in good yields.The 4-methylumbelliferyl α-ketoside, the standard substrate for neuraminidase, was prepared in a yield of up to 70percent.New Neu5Ac ketosides were prepared with fluorescein and the fluorescein analog, 2-methyl-6-hydroxyfluoran (2-methyl-6-hydroxyxanthene-9-spiro-1'-isobenzofuran-3'-one) as aglycons, the latter being synthesized from 2-(2-hydroxy-5-methylbenzoyl) benzoic acid and 3-fluorophenol.The α configuration was ascertained by 400-MHz 1H-NMR spectroscopy and by cleavage of the ketosides with neuraminidases from Vibrio cholerae and Clostridium perfringens.The enzymic hydrolysis of the 2-methylfluoran-6-yl ketoside gave Km values of 82 μM (V. cholerae) and 96 μM (C. perfringens).