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Synthesis of Glycosylrifamycins, a new type of semisynthetic rifamycins
Author(s) -
Bartolucci Cecilia,
Cellai Luciano,
Martuccio Concetta,
Rossi Andrea,
Segre Anna Laura,
Savu Simona Rizea,
Silvestro Luigi
Publication year - 1996
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.19960790611
Subject(s) - chemistry , rifamycin , stereochemistry , shikimic acid , glycosyl , acetylation , combinatorial chemistry , antibiotics , organic chemistry , biochemistry , gene
Glycosylrifamycins, a new type of semisynthetic rifamycin derivatives, can be easily obtained by reaction of 3‐(2‐aminoethylthio)rifamycin SV ( 2 ) with a glycosyl compound carrying a coupling group, such as isothicyanate or carboxy. We prepared O ‐acetylated and free glucopyranosyl and arabinopyranosyl derivatives of rifamycin S and SV (see 3–10 ). Additionally, derivatives with D ‐saccharo‐1,4‐lactone and with shikimic acid were obtained (see 11–15 ). Glycosylrifamycins show an interesting inhibitory power on Gram ‐positive bacteria ( Table ).