Synthesis of sialic acid-containing nucleotide sugars: CMP-sialic acid analogs.
Syntheses of some sialic acid-containing nucleotide sugars are reported. The reaction of methyl [(2-hydroxy)ethyl 5-acetamido-4,7,8,9-tetra-O-acetyl-3,5-dideoxy-D-glycero-alpha-D-galacto -2-nonulopyranosid]onate (4) with various fully protected hydrogen phosphonates of nucleosides (5a-c) in the presence of 2,4,6-triisopropylbenzenesulfonyl chloride (TPSCl), gave, after oxidation and deprotection, the corresponding sialic acid-containing nucleotide sugar analogs (8a-c).
Ikeda
K
K
School of Pharmaceutical Sciences, University of Shizuoka, Japan.
Nagao
Y
Y
Achiwa
K
K
D000998:Antiviral Agents / Q000138:chemical synthesis; D003568:Cytidine Monophosphate / Q000031:analogs & derivatives*; D054306:Dideoxynucleotides; D019158:N-Acetylneuraminic Acid; D000216:N-Acylneuraminate Cytidylyltransferase / Q000037:antagonists & inhibitors; D012794:Sialic Acids / Q000737:chemistry*; D012799:Sialyltransferases / Q000037:antagonists & inhibitors; D013938:Thymidine Monophosphate / Q000031:analogs & derivatives*; D013942:Thymine Nucleotides / Q000737:chemistry*; D015215:Zidovudine / Q000031:analogs & derivatives* / Q000737:chemistry
D000998:Antiviral Agents; D054306:Dideoxynucleotides; D012794:Sialic Acids; D013942:Thymine Nucleotides; C057287:3'-azido-3'-deoxythymidine 5'phosphate; D013938:Thymidine Monophosphate; D015215:Zidovudine; D012799:Sialyltransferases; D000216:N-Acylneuraminate Cytidylyltransferase; D003568:Cytidine Monophosphate; D019158:N-Acetylneuraminic Acid