Formation of gutingimycin: analytical investigation of trioxacarcin A-mediated alkylation of dsDNA.
Formation and fragmentation of recognition complexes between trioxacarcin A and various DNA sequences were examined by temperature-dependent UV and CD spectroscopy, HPLC analysis, and ESI mass spectrometry with regard to reaction conditions, intermediates, products, mechanism, and sequence specificity. Cleavage of the trioxacarcin-DNA complexes provided the natural product gutingimycin by guanine abstraction. The resulting DNA with an abasic site was further cleaved into a DNA fragment with a furanyl unit at the 3'-end and an oligonucleotide with a phosphorylated 5'-end.
Fitzner
Ansgar
A
Institut für Organische und Biomolekulare Chemie, Georg-August-Universität Göttingen, Tammannstr. 2, 37077, Göttingen, Germany.
Frauendorf
Holm
H
Laatsch
Hartmut
H
Diederichsen
Ulf
U
D000478:Alkylation; D000617:Aminoglycosides / Q000737:chemistry*; D000873:Anthracenes / Q000138:chemical synthesis*; D001483:Base Sequence; D002851:Chromatography, High Pressure Liquid; D002942:Circular Dichroism; D004247:DNA / Q000737:chemistry*; D004187:Disaccharides / Q000138:chemical synthesis*; D007700:Kinetics; D021241:Spectrometry, Mass, Electrospray Ionization; D013056:Spectrophotometry, Ultraviolet
D000617:Aminoglycosides; D000873:Anthracenes; D004187:Disaccharides; C495808:gutingimycin; C033790:trioxacarcin; D004247:DNA