101554-19-2Relevant academic research and scientific papers
Accessibility of N-acyl-D-mannosamines to N-acetyl-D-neuraminic acid aldolase
Pan, Yanbin,Ayani, Tiffany,Nadas, Janos,Wen, Shouming,Guo, Zhongwu
, p. 2091 - 2100 (2007/10/03)
N-Acetyl-D-neuraminic acid (NeuNAc) aldolase is an important enzyme for the metabolic engineering of cell-surface NeuNAc using chemically modified D-mannosamines. To explore the optimal substrates for this application, eight N-acyl derivatives of D-mannos
5-azido derivatives of neuraminic acid - Synthesis and structure
Schneider, Regine,Freyhardt, Clemens C.,Schmidt, Richard R.
, p. 1655 - 1661 (2007/10/03)
Benzyl sialoside 1 was transformed into the corresponding 5-azido derivative 4 by N-nitrosation of the 5-acetylamino group and treatment with base followed by hydrazoic acid or, alternatively, by N,O-deacetylation followed by diazo group transfer to the amino moiety by means of TfN3. Regioselective 4-O-acetylation and introduction of the MPM group at 9-O afforded glycosyl acceptor 11. N,O-Deacetylation of ethyl 2-thiosialoside 13 afforded 14 which, after diazo group transfer to the amino group, furnished 5-azido derivative 16, which can serve as a sialyl donor. Activation of the ethylthio leaving group in the absence of an acceptor afforded 2,3-dehydro derivative 17. Regioselective 4-O-acetylation and 9-O-benzylation furnished glycosyl acceptor 22. An X-ray analysis was obtained from crystals of the 7,8,9-O-unprotected intermediate 21.
Synthesis of N-glycolyl-8-o-sulfoneuraminic acid
Tanaka,Kai,Sun,Takayanagi,Furuhata
, p. 2095 - 2098 (2007/10/03)
N-Glycolyl-8-O-sulfoneuraminic acid (1) was synthesized for the first time in good yield. The key intermediates for synthesis of 1, neoraminic acid O- benzyl α-glycoside (3) and neuraminic acid S-methyl α-glucoside (10) were prepared from readily availabl
Synthesis of fluorescent 4-methyl-7-thiocoumaryl S-glycosides of sialic acid
Tanaka,Kai,Sun,Takayanagi,Uda,Furuhata
, p. 1844 - 1848 (2007/10/03)
Condensation of 4-methyl-7-thiocoumarin sodium salt with methyl 5-N- acetyl-4,7,8,9-tetra-O-acetyl-2-chloro-2,3,5-trideoxy-D-glycero-D-galacto-2- nonulopyranosonate (2), methyl 5-N-(O-acetylglycolyl)-4,7,8,9-tetra-O- acetyl-2-chloro-2,3,6-trideoxy-D-glyce
A simple procedure for the synthesis of the methyl and benzyl glycosides of Neu5Ac and 4-epi-Neu5Ac. Conversion of the benzyl and methyl glycosides of Neu5Ac into N-trifluoroacetylneuraminic acid benzyl glycosides
Byramova, Nargiz E.,Tuzikov, Alexander B.,Bovin, Nicolai V.
, p. 161 - 176 (2007/10/02)
From the reaction products of the Kuhn-Bashang synthesis of Neu5Ac, 5-acetamido-3,5-dideoxy-α- and -β-D-glycero-D-talo-2-nonulopyranosonic acid (4-epi-Neu5Ac) were isolated as the acetylated methyl esters (1 and 2).Treatment of methyl (5-acetamido-4,7,8,9
