130525-59-6Relevant articles and documents
Structural Variations on N-Acetylneuraminic Acid, 20. Synthesis of Some 2,3-Didehydro-2-deoxysialic Acids Structurally Varied at C-4 and Their Behavior towards Sialidase from Vibrio cholerae
Schreiner, Erwin,Zbiral, Erich,Kleineidam, Reinhard G.,Schauer, Roland
, p. 129 - 134 (2007/10/02)
The peracetylated methyl ester 1 of N-acetylneuraminic acid was transformed into the oxazoline derivative 2, which was hydrogenated with Pd/C/H2 to give the 4-deoxy-Neu5Ac2en derivative 3.Acid cleavage of the oxazoline 2 by trifluoroacetic acid (THF) gave the 4-epi-Neu5Ac2en derivative 4a, which was saponified to the known 4-epi-Neu5Ac2en 4b.Treatment of 4a with triphenylphosphane/diethylazodicarboxylate (DEAD)/HN3 in toluene gave the 4-azido-4-deoxy-Neu5Ac2en derivative 5a as well as the 4-epi-azido-4-deoxy-Neu5Ac2en derivative 6a.Both epimers could be saponified yielding the free dehydrosialic acid derivatives 5b and 6b.Furthermore, 4-formamido-4-deoxy-Neu5Ac2en 7b was prepared via the derivative 7a, which was formed from 5a by reaction with triphenylphosphane/formyl acetate.In addition, the free dehydrosialic acid derivatives 5b and 6b were transformed into the stable P-N ylides 8 and 10, but only 8 could be hydrolyzed to the triethylammonium salt of 4-amino-4-deoxy-Neu5Ac2en 9a, which was converted into the zwitterionic compound 9b.Finally 4-acetamido-4-deoxy-Neu5Ac2en 11c was prepared from 4-acetamido-4-deoxy-N-acetylneuramic acid 10 via the derivatives 11a and 11b by well-known methods.The compounds 4b, 5b, 6b, 7b, 9b, and 11c were investigated as inhibitors of Vibrio cholerae sialidase, and their Ki values were determined.
