Nonulopyranosonic acid

CuH19N09 2H20 Sialic acid dihydrate N-acetylneuraminic acid dihydrate 5-acetamido-3,5-dideoxy-/3-D-gli/c-ero-D-gfliocto-nonulopyranosonic acid dihydrate17... 

D. C. M. Kong and M. von Itzstein, The first synthesis of a C-7 nitrogen-containing sialic acid analogue, 5-acetamido-7-azido-3,5,7-trideoxy-D-giycero-D-ga/acro-2-nonulopyranosonic acid (7-azido-7-deoxy-Neu5Ac), Tetrahedron Lett. 36 957 (1995). 

Figure 4. Sialic acid aldolase-catalyzed synthesis of fluorosialic acid and related substances, (a) Normal reaction, (b) synthesis of 9-fluoro-9-deoxy-N-acetylneuraminic acid, (c) synthesis of 7,9-difluoro-7,9-dideoxy-D-g/ycero-L-a-a/tro-2-nonulopyranosonic acid, (d) synthesis of S-fluoro-3,5-dideoxy-D-g/ycero-a-D-gu/o-2-nonuIopyranosonic acid...

Amino-3,5-dideoxy-D-gZt/cero-re-D-gaZacto-nonulopyranosonic acid (Neuraminic acid)... 

NeuAc aldolase, or sialic acid aldolase, catalyzes the reversible condensation of pyruvate with N-acetylmannosamine (ManNAc) to form NeuAc (sialic acid N-acetyl-5-amino-3,5-dideoxy-D-g ycero-D-ga acto-2-nonulopyranosonic acid) (Fig. 14.1-... 

Acetylamino)-3,5-dideoxy-D-g/ycero-p-D-ga/ac/o-2-nonulopyranosonic acid 2-(hydrogen 5 -cytidylate), A-21... 

In the area of ulosonic acids, condensation of D-mannose with oxalacetic acid gave 3-deoxv-D-alycero-D-aalacto-2-nonulopyranosonic acid from which a protected glycosyl bromide and hence glycosides e.g. (7) were prepared,and the phenylthioglycosides (8), made from tri-Q-benzyl-D-glucal, can be converted into Q-glycosides. ... 

Besides the 0-glycosides mentioned so far, also attention has been paid to the synthesis of N- and S-analogues. The p-nitrophenyl N-glycoside of a-N-acetylneuraminic acid has been prepared by silver carbonate-promoted reaction of 4,7,8,9-tetra-0-acetyl-2-chloro-2-deoxy-p-N-acetylneuraminic acid methyl ester with p-nitroaniline and subsequent deprotection (Privalova and Khorlin 1969). Treatment of the same precursor with sodium azide, followed by de-esterification, led to the formation of 2-azido-2-deoxy-a-N-acetylneuraminic acid (Supp et al. 1980). The same authors reported also the preparation of the p-form. The azides can readily be converted into the 2-amino derivatives of N-acetylneuraminic acid. Subsequently, the amino function has been benzoylated. Data on the syntheses of the methyl and p-nitrophenyl S-glycosides of a-N-acetylneuraminic acid have been presented by Privalova and Khorlin (1969), whereas Ponpipom et al. (1980) have described a method for the synthesis of 5-acetamido-2-S-[6-(5-cholesten-3p-yloxy)hexyl]-3,5-dideoxy-2-thio-p-D-g/vccro-D-ga/acto-2-nonulopyranosonic acid. 

Ci2H21N09 H20 Sialic acid, methyl ester, monohydrate N-ace-tylneuraminic acid, methyl ester, monohydrate methyl 5-acetamido-3,5-dideoxy-/3-i>g/ycero-D-gaiacto-nonulopyranosonate monohydrate19... 

Methyl 5-acetamido-3,5-dideoxy-D-glycero- -D-galocto-nonulopyranosonate, monohydrate (N-acetylneuraminic acid, methyl ester, monohydrate sialic acid, methyl ester, monohydrate)... 

Also attention has been paid to the synthesis of sialodisaccharides, having sialic acid in reducing position. By condensation of tetra-O-acetyl-a-D-glucopyranosyl bromide or tetra-O-acetyl-a-D-galactopyranosyl bromide with methyl 5-acetamido-2,4,7,8-tetra-0-acetyl-3,5-dideoxy-9-0-trityl-D-g/> c ro-D-ga/ac/o-2-nonulopyranosonate in nitromethane under the influence of silver perchlorate, followed by 0-deacetylation, the methyl esters of the corresponding (5(1 9) disaccharides were obtained in 67 and 46% yield, respectively (Khorlin and Privalova 1968). 

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