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Digitoxosyltetracenomycin C and Glucosyltetracenomycin C, Two Novel Elloramycin Analogues Obtained by Exploring the Sugar Donor Substrate Specificity of Glycosyltransferase ElmGT
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posted on 2002-09-05, 00:00 authored by Carsten Fischer, Leticia Rodríguez, Eugenio P. Patallo, Fredilyn Lipata, Alfredo F. Braña, Carmen Méndez, Jose A. Salas, Jürgen RohrOur explorations of glycosyltransferase ElmGT from Streptomyces olivaceus Tü 2353, which shows an
interesting flexibility regarding its sugar donor substrate, were extended toward various previously
unexplored sugar co-substrates. The studies revealed that ElmGT, which normally transfers l-rhamnose
to 8-demethyltetracenomycin C as a crucial biosynthetic step in elloramycin biosynthesis, is also able to
process an activated non-deoxygenated sugar, NDP-d-glucose, as well as NDP-l-digitoxose, which is the
first example of an NDP-l-sugar co-substrate of ElmGT possessing an axial 3-OH group. The structures
of the resulting novel elloramycin analogues of these experiments, 8-demethyl-8-l-digitoxosyltetracenomycin C (4) and 8-demethyl-8-d-glucosyltetracenomycin C (7), were elucidated mainly by 1H and 13C
NMR spectroscopy and by mass spectrometry.
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biosynthetic stepmass spectrometryNovel Elloramycin Analogues ObtainedSugar Donor Substrate Specificity13 C NMR spectroscopyGlucosyltetracenomycin Csugar donor substrateglycosyltransferase ElmGTnovel elloramycin analoguesdemethyl1 HDigitoxosyltetracenomycin CGlycosyltransferase ElmGTOHelloramycin biosynthesis
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