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Strukturmodifizierte Isokalafungine und Isonanaomycine
Author(s) -
Hoffmann Bernd,
Lackner Helmut
Publication year - 1994
Publication title -
liebigs annalen
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 0947-3440
DOI - 10.1002/jlac.199519950113
Subject(s) - chemistry , chromophore , stereochemistry , quinone , computational chemistry , organic chemistry
Structurally Modified Isokalafungins and Isonanaomycins The total synthesis of structural analogues of the unnatural, C‐6‐hydroxylated isokalafungins and isonanaomycins is described. The new compounds show improved antibiotic activity and support theories for a mechanism of action which base on the formation of reactive quinone methides. Calculations of the molecular structures show that the chromophore of the most active 9‐methyl derivatives 28 and 32 is bended off along its 5‐CO‐10‐CO axis. This corresponds to an unusual shifting of characteristic 13 C‐NMR signals. Different experiments for the introduction of X‐CH 2 ‐ or sugar residues into 1 (e.g. isolactoquinomycins) demonstrate the limits of the general synthetic pathway. Finally a short overview on significant structure/activity relationships in the (iso)nanaomycin D field is given.