Digitoxosyltetracenomycin C and Glucosyltetracenomycin C, Two Novel
Elloramycin Analogues Obtained by Exploring the Sugar Donor Substrate
Specificity of Glycosyltransferase ElmGT
Carsten Fischer
Leticia Rodríguez
Eugenio P. Patallo
Fredilyn Lipata
Alfredo F. Braña
Carmen Méndez
Jose A. Salas
Jürgen Rohr
10.1021/np020112z.s001
https://acs.figshare.com/articles/journal_contribution/Digitoxosyltetracenomycin_C_and_Glucosyltetracenomycin_C_Two_Novel_Elloramycin_Analogues_Obtained_by_Exploring_the_Sugar_Donor_Substrate_Specificity_of_Glycosyltransferase_ElmGT/3734313
Our explorations of glycosyltransferase ElmGT from <i>Streptomyces olivaceus </i>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 (<b>4</b>) and 8-demethyl-8-d-glucosyltetracenomycin C (<b>7</b>), were elucidated mainly by <sup>1</sup>H and <sup>13</sup>C
NMR spectroscopy and by mass spectrometry.
2002-09-05 00:00:00
biosynthetic step
mass spectrometry
Novel Elloramycin Analogues Obtained
Sugar Donor Substrate Specificity
13 C NMR spectroscopy
Glucosyltetracenomycin C
sugar donor substrate
glycosyltransferase ElmGT
novel elloramycin analogues
demethyl
1 H
Digitoxosyltetracenomycin C
Glycosyltransferase ElmGT
OH
elloramycin biosynthesis