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Carbocyclic Analogues of N ‐Acetyl‐2,3‐didehydro‐2‐deoxy‐ D ‐neuraminic Acid (Neu5Ac2en, DANA): Synthesis and Inhibition of Viral and Bacterial Neuraminidases
Author(s) -
Vorwerk Steffen,
Vasella Andrea
Publication year - 1998
Publication title -
angewandte chemie international edition
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 5.831
H-Index - 550
eISSN - 1521-3773
pISSN - 1433-7851
DOI - 10.1002/(sici)1521-3773(19980703)37:12<1732::aid-anie1732>3.0.co;2-i
Subject(s) - neuraminic acid , stereochemistry , chemistry , neuraminidase , biochemistry , biology , sialic acid , enzyme
Inhibition of neuraminidases from Influenza A and Salmonella typhimurium is shown by the carbocyclic compound 2 , whereas its double‐bond isomer 1 hardly binds to these enzymes. The cyclohexenes 1 and 2 were prepared from N ‐acetyl‐ D ‐mannosamine in 18 steps in 2.6 and 1.6 % yields, respectively.