10.1021/np020112z.s001
Carsten Fischer
Carsten
Fischer
Leticia Rodríguez
Leticia
Rodríguez
Eugenio P. Patallo
Eugenio P.
Patallo
Fredilyn Lipata
Fredilyn
Lipata
Alfredo F. Braña
Alfredo F.
Braña
Carmen Méndez
Carmen
Méndez
Jose A. Salas
Jose A.
Salas
Jürgen Rohr
Jürgen
Rohr
Digitoxosyltetracenomycin C and Glucosyltetracenomycin C, Two Novel
Elloramycin Analogues Obtained by Exploring the Sugar Donor Substrate
Specificity of Glycosyltransferase ElmGT
American Chemical Society
2002
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
2002-09-05 00:00:00
Journal contribution
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.