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Synthesis and Biological Properties of N ‐Acetyl‐4‐deoxy‐ D ‐neuraminic Acid
Author(s) -
Hagedorn HeinzWerner,
Brossmer Reinhard
Publication year - 1986
Publication title -
helvetica chimica acta
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.74
H-Index - 82
eISSN - 1522-2675
pISSN - 0018-019X
DOI - 10.1002/hlca.19860690837
Subject(s) - chemistry , sialidase , neuraminic acid , cleavage (geology) , stereochemistry , medicinal chemistry , mesylate , catalysis , organic chemistry , biochemistry , sialic acid , enzyme , neuraminidase , geotechnical engineering , fracture (geology) , engineering
N ‐Acetylneuraminic acid ( 1 ) can be transformed into the methyl α‐ D ‐ketoside 2 which, by reaction with methanesulfonyl chloride, yields the corresponding 4‐ O ‐mesylate 3 and the 4,7‐di‐ O ‐mesylate 4 as a by‐product. Compound 3 reacts with Nal giving the 4‐deoxy‐4‐iodo compound 5 with equatorial orientation of the I‐atom. As second product, the dihydrooxazole 6 is produced. Catalytic hydrogenation of 5 is followed by ester cleavage and removal of the isopropylidene group yielding the methyl α‐ D ‐ketoside 8 which affords the title compound, N ‐acetyl‐4‐deoxyneuraminic acid ( 9 ), by reaction with fowl plague virus sialidase. Further biochemical activities of 8 and 9 are reported.