Premium
Selective Derivatization of the Ionophore X‐206 at C(22) Maintaining Potassium Binding
Author(s) -
O'Sullivan Anthony C.,
Struber Fritz
Publication year - 1998
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.19980810503
Subject(s) - chemistry , derivatization , ionophore , potassium , metal , metal ions in aqueous solution , medicinal chemistry , stereochemistry , organic chemistry , high performance liquid chromatography , calcium
The insecticidal polyether antibiotic X‐206 ( 1 ) complexes potassium ions using nearly all of its O‐atoms either for binding to the metal ion or for participation in a H‐bonding network which helps to hold X‐206 in the ionophoric tertiary structure. The group OHC(22) is not involved in these processes. It was supposed that derivatization of this group would not affect the ionophoric properties and would produce insecticidally active compounds. The chemistry leading to selective modification of OHC(22) via the intermediate 6 was developed. The potassium‐binding properties and insecticidal activities of the MeCOOC(22) and MeOC(22) compounds 3 and 11 , respectively, confirmed that derivatization of the peripheral OHC(22) was a valid strategy for the synthesis of biologically active compounds.