Solid-phase synthesis of bleomycin group antibiotics. Elaboration of deglycobleomycin A(5).
The solid-phase syntheses of two deglycobleomycin A(5) analogues were achieved using a commercially available polystyrene resin containing triphenylmethyl-linked spermidine. The final products were deblocked and released from the resin, analyzed, and purified by C(18) reversed phase HPLC and characterized by high-field (1)H NMR spectroscopy and mass spectrometry. The purified products relaxed supercoiled plasmid DNA in a concentration-dependent fashion and to the same extent as authentic material derived from natural BLM A(5).
Leitheiser
C J
CJ
Departments of Chemistry and Biology, University of Virginia, Charlottesville, Virginia 22901, USA.
Rishel
M J
MJ
Wu
X
X
Hecht
S M
SM
D001761:Bleomycin / Q000031:analogs & derivatives* / Q000138:chemical synthesis / Q000737:chemistry / Q000494:pharmacology; D002851:Chromatography, High Pressure Liquid; D004278:DNA, Superhelical / Q000187:drug effects; D009682:Magnetic Resonance Spectroscopy; D013058:Mass Spectrometry; D015394:Molecular Structure
D004278:DNA, Superhelical; D001761:Bleomycin; C033284:deglycobleomycin