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
- 12 February 1991
- journal article
- research article
- Published by Wiley in European Journal of Organic Chemistry
- Vol. 1991 (2), 129-134
- https://doi.org/10.1002/jlac.199119910124
Abstract
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 PN 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 zwitter ionic compound 9b. Finally 4-acetamido-4-deoxy-Neu5Ac2en 11e was prepared from 4-acetamido-4-deoxy-N-acetylneuraminic 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.Keywords
This publication has 20 references indexed in Scilit:
- Synthese von Glycofuranosylformamiden, -isocyaniden und -isocyanaten ausgehend von den entsprechenden GlycosylazidenEuropean Journal of Organic Chemistry, 1988
- Synthesis and Biological Properties of N‐Acetyl‐4‐deoxy‐D‐neuraminic AcidHelvetica Chimica Acta, 1986
- 4‐Methylumbelliferyl 5‐Acetamido‐3,4,5‐trideoxy‐α‐D‐manno‐2‐nonulopyranosidonic Acid: Synthesis and Resistance to Bacterial SialidasesHelvetica Chimica Acta, 1986
- Deoxy‐nitrosugars. 16th Communication. Synthesis of N‐acetyl‐4‐deoxyneuraminic acidHelvetica Chimica Acta, 1986
- The Action of Sialidases on Substrates ContainingO-Acetylsialic AcidsBiological Chemistry Hoppe-Seyler, 1986
- Rapid chromatographic technique for preparative separations with moderate resolutionThe Journal of Organic Chemistry, 1978
- Carbon-13 nuclear magnetic resonance spin-lattice relaxation in the N-acylneuraminic acids. Probes for internal dynamics and conformational analysisJournal of the American Chemical Society, 1977
- Reaktionen mit phosphororganischen Verbindungen. XLI[1]. Neuartige synthetische Aspekte des Systems Triphenylphosphin‐Azodicarbonsäureester‐HydroxyverbindungHelvetica Chimica Acta, 1976
- Stability constants for the complexation of alkali and alkaline‐earth cations byN‐acetyl‐neuraminic acidFEBS Letters, 1972
- Zur Wirkungsspezifität der Neuraminidase. Das Verhalten isomerer N.O-Diacetyl-neuraminsäureglykoside im Submaxillarismucin von Pferd und Rind bei Einwirkung bakterieller NeuraminidaseHoppe-Seyler´s Zeitschrift Für Physiologische Chemie, 1968