Synthesis of a doubly labelled concanamycin derivative for ATPase binding studies

Autor(en): Ingenhorst, G
Bindseil, KU
Boddien, C
Drose, S
Gassel, M
Altendorf, K 
Zeeck, A
Stichwörter: BAFILOMYCINS; Chemistry; Chemistry, Organic; enzymes; INHIBITORS; iodine; MICROORGANISMS; natural products; P-TYPE; photoaffinity labelling; UNUSUAL MACROLIDES; V-TYPE
Erscheinungsdatum: 2001
Herausgeber: WILEY-V C H VERLAG GMBH
Journal: EUROPEAN JOURNAL OF ORGANIC CHEMISTRY
Volumen: 2001
Ausgabe: 23
Startseite: 4525
Seitenende: 4532
Zusammenfassung: 
The synthesis of a doubly labelled concanamycin derivative for binding studies with V- and P-type ATPases is described. The starting point was 21-deoxyconcanolide A (6), which was generated from concanamycin A (1) in three steps and which exhibited the full ATPase inhibitor activity, with the advantage of a stability better than that of 1. Through use of a suitable protecting group for 6, the carbene-generating diazirine residue and I-125 were introduced regio- and stereo- selectively. The inhibitory efficacy of the resulting 23-iodo(I-125)-9-O-[p-(trifluoroethyldiazirinyl)benzoyl]-21,23- dideoxyconcanolide A (11b) turned out to be high enough for labelling studies. Photoaffinity labelling experiments clearly showed that 11b is a suitable derivative with which to determine the binding site of concanamycin-like compounds in different ATPases.
ISSN: 1434193X

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