V-Acetylneuraminic acid

Deoxy-D- /rce/ o-D- a/ac7i7-nonulosonie Acid (KDN) V-Acetylneuraminic Acid Aldolase Catalyzed Preparative Aldol Additions with Pyruvate Typical Procedure27 ... 

Vasella has used deoxy-nitro sugars for the synthesis of various biologically important carbohydrates,10 and the radical nitromethylation of deoxy-nitro sugars has been used for synthesis of fructose 6-phosphate11 and 6-C-methyl and 6-C-(hydroxymethyl)analogues of V-acetylneuraminic acid (see Scheme 7.2).12... 

Misaki, R., Fujiyama, K. and Seki, T. (2006) Expression of human CMP-V-acetylneuraminic acid synthetase and CMP-sialic acid transporter in tobacco suspension-cultured cell. Biochemical and Biophysical Research Communications, 339 (4), 1184—1189. 

Aldulosonic acids are involved in many important areas of glycobiology and glycomedicine, such as /V-acetylneuraminic acid (Neu5Ac), 3-deoxy-D-glycero-v-galacto-non-2- Aosonic acid (Kdn) and 3-deoxy-D-manno-oct-2-ulosonic acid (Kdo). 

The Sowden homologation [21], based on the nitroaldol condensation (Henry reaction) [22] between the aldehydo sugar and nitromethane in basic medium, followed by the Nef decomposition [23] of the resultant nitronate in strongly acidic conditions, has been employed in a more limited number of cases than the cyanohydrin synthesis. A recent example in this area is shown by the stepwise homologation of (V-acetyl-D-mannosamine (11) into /V-acetylneuraminic acid (12) [24] (Scheme 4). Also, this procedure has found... 

Having set up a protocol for the aminohomologation of various aldehydo sugars, the value of the method was tested by the synthesis of simple natural products. The firsl example involved [57a] the conversion of 2,3 4,5-di-0-isopropylidene-D-arabinose 59 (Scheme 18) through the nitrone 60 into the W-acetyl-D-mannosamine diacetonide 61 and the deprotected compound 11, both well-known key intermediates for the synthesis of /V-acetylneuraminic acid (Neu5Ac) [59,60]. Unfortunately, in this case the addition of 2-LTT (25b) to the nitrone 60 occurred with modest selectivity (ds 75% to the best) therefore, the overall yield of 61 was quite low (29%). 

L. Benzing-Nguyen and M. B. Perry, Stepwise synthesis of /V-acetylneuraminic acid and /V-acety 1 - K ncuraminic acid, J. Org. Chem. 73 551 (1978). 

R. Csuk, M. Hugener, and A. Vasella, A new synthesis of /V-acetylneuraminic acid, Helv. Chim. Acta 71 609 (1988). 

Sialyl residues in oligosaccharides are introduced by the reaction of cyti-dine monophosphate-V-acetylneuraminic acid (49) as the sugar donor with the appropriate substrate, in the presence of specific transferases. Three of these have been utilized in syntheses which may be considered to be preparative. None are readily available. The most common, which we have called STA (see Table I), catalyzes the transfer of a 5-acetamido-3,5-di-deoxy-D-g/ycm>-a -D-ga/arfo-2-hexulopyranosonic acid unit (the a-D-pyra-nose form of JV-acetylneuraminic acid) to the primary position of D-galactose in a JV-acetyllactosamine residue.86 This enzyme also transfers vV-acetyl-9-O-acetylneuraminic acid (20) and V-glycolylneuraminic acid (12) from the corresponding cytidine monophosphate derivatives.16 The commercial enzyme is rather expensive, but pork liver from a butcher is a... 

U. Nohle, J. M. Beau, and R. Schauer, Uptake, metabolism and excretion of orally and intravenously administered, double-labeled V-glycoloylneuraminic acid and single-labeled 2-deoxy-2,3-dehydro-V-acetylneuraminic acid in mouse and rat, Eur. J. Biochem., 126 (1982) 543-548. 

M. von Itzstein, W. Y. Wu, and B. Jin, The synthesis of 2,3-didehydro-2,4-dideoxy-4-guanidinyl-V-acetylneuraminic acid A potent influenza virus sialidase inhibitor, Carbohydr. Res., 259 (1994) 301-305. 

I. D. Starkey, M. Mahmoudian, D. Noble, P. W. Smith, P. Cherry, P. D. Howes, and S. L. Sollis, Synthesis and influenza virus sialidase inhibitory activity of the 5-desacetamido analog of 2,3-didehydro-2,4-dideoxy-4-guanidinyl-V-acetylneuraminic acid (GG167), Tetrahedron Lett., 36 (1995) 299-302. 

Acid treatment of the carboxyl-reduced derivative of /V-acetylneuraminic acid yields the 2,7-anhydride of the corresponding non-2-ulopyranose.268... 

By analogy with the synthesis of /V-acetylneuraminic acid,63 di-A-acetyl derivatives of 5,7-diamino-3,5,7,9-tetradeoxynon-2-ulosonic acids could be obtained by condensation of 2,4-diacetamido-2,4,6-trideoxyhexoses with oxaloacetic acid under basic conditions. Four chiral centers in the C precursors, C-2 C-5, correspond to the centers C-5-C-8 in the target C9 products, and the fifth asymmetric center, C-4, is formed upon condensation. At present, derivatives of twelve 2,4-diamino-2,4,6-trideoxy-hexoses with the d-gluco, o-manno, L-allo, r>-galacto, D- and L-altro, D- and L-talo, D- and l-gulo, D- and L-ido configurations have been prepared by multistep chemical syntheses.11,17,18,64,65... 

Hex hexose, HexNAc /V-acetylhexosamine, Neu5Ac /V-acetylneuraminic acid, dHex deoxyhexose. This table is adapted from ref. 96. 

A preparation of colominic acid [poly-(V-acetylneuraminic acid)] prepared from a culture filtrate of a certain strain of Escherichia coli could be fractionated by ion-exchange chromatography into several fractions containing ultraviolet-absorbing material. One fraction contained uridine pjTophosphate linked to a neuraminic peptide. It is suggested that the... 

The final step in a synthesis of cytidine-5 -monophosphono-J/V-acetylneuraminic acid (CMP-Neu5Ac) [27 4, Scheme 7.27] illustrates the global deprotection of... 

Cytidine monophosphate-sialic acid synthetase (EC 2.7.7.43) catalyzes the activation of /V-acetylneuraminic acid (NANA) by CTP to form CMP-NANA. 

The most representative example of this family is /V-acetylneuraminic acid (NeuSAc 1 Scheme 2), a nine-carbon sugar, ubiquitous in the animal kingdom and especially... 

Anhydro-/V-acetylneuraminic acid Edible bird s nest... 

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