𝔖 Bobbio Scriptorium
✦   LIBER   ✦

Structural Variations ofN-Acetylneuraminic Acid, 7. Synthesis of the C-7-, C-8-, and C-7,8-Side Chain Epimers of 2-Deoxy-2,3-didehydro-N-acetylneuraminic Acid and Their Behaviour Towards Sialidase fromVibrio cholerae

✍ Scribed by Zbiral, Erich ;Brandstetter, Hannelore H. ;Christian, Rudolf ;Schauere, Roland

Publisher
John Wiley and Sons
Year
1987
Tongue
English
Volume
1987
Category
Article
ISSN
0947-3440

No coin nor oath required. For personal study only.

✦ Synopsis

Thl: perawtylstcd mcthyl cstcr dcrivativcs of 7-rpi-i-NeuSAc (ta), H-epi-NeuSAc (3 a), and 7.8-bis-epi-NcuSAc (4 a) wcrc transformed hy trimcihylsilyl trifluoromethanesulronale into the corrcsponding 2-cieoxy-2,3-didehydro derivatives 2b-4 b. As minor products the 4.5-osazolino derivatives 5 b rind 6 b are formed. Hydrolysis of 2 b-4b yields the frce acids 7-epCNeuSAc2cne (2e), &pi-NcuShc2ene (3c). and 7.8-bis-epi-Neu5Ac2cnc (4c). These show significantly diffcrcnt inhibitory influcnces on the hydrolysis of 4-mcthylumbcll~ery I-u-NcuSAc by Vibrio choferm sialidase. This was the reason for esiablishing the conformation of 2c-4c and of the wcli-known 2-dcoxy-2.3-didehydro-N-acc~ylneuramioic acid (NeuMcZcnc) ( 1 ~) . A signillcant relationship between [he clwacicristic prohtes of the u-side of lc-4c and thc inhence an the ciizyrnc rcaclion was round.

πŸ“œ SIMILAR VOLUMES

Structural Variations ofN-Acetylneuramin
Structural Variations ofN-Acetylneuraminic Acid, 11, Synthesis of the 4-Methylumbelliferyl 2Ξ±-Glycosides of 7-Epi-, 8-Epi-, and 7,8-Bis(epi)-N-acetylneuraminic Acids, as well as of 7-Deoxy-, 8-Deoxy-, 9-Deoxy-, and 4,7-Dideoxy-N-acetylneuraminic Acids and Their Behaviour Towards Sialidase fromVibrio cholerae
✍ Zbiral, Erich ;Schreiner, Erwin ;Salunkhe, Mamikrao M. ;Schulz, Gerhard ;Kleinei πŸ“‚ Article πŸ“… 1989 πŸ› John Wiley and Sons 🌐 English βš– 942 KB
Structural Variations on N-acetylneurami
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 πŸ“‚ Article πŸ“… 1991 πŸ› John Wiley and Sons 🌐 English βš– 652 KB

## Abstract The peracetylated methyl ester 1 of N‐acetylneuraminic acid was transformed into the oxazoline derivative 2, which was hydrogenated with Pd/C/H~2~ to give the 4‐deoxy‐Neu5Ac2en derivative 3. Acid cleavage of the oxazoline 2 by trifluoroacetic acid (THF) gave the 4‐epi‐Neu5Ac2en derivati