TY - JOUR
T1 - Digitoxosyltetracenomycin C and glucosyltetracenomycin C, two novel elloramycin analogues obtained by exploring the sugar donor substrate specificity of glycosyltransferase ELmGT
AU - Fischer, Carsten
AU - Rodríguez, Leticia
AU - Patallo, Eugenio P.
AU - Lipata, Fredilyn
AU - Braña, Alfredo F.
AU - Méndez, Carmen
AU - Salas, Jose A.
AU - Rohr, Jürgen
PY - 2002/11
Y1 - 2002/11
N2 - Our 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.
AB - Our 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.
UR - http://www.scopus.com/inward/record.url?scp=0036854694&partnerID=8YFLogxK
UR - http://www.scopus.com/inward/citedby.url?scp=0036854694&partnerID=8YFLogxK
U2 - 10.1021/np020112z
DO - 10.1021/np020112z
M3 - Article
C2 - 12444703
AN - SCOPUS:0036854694
SN - 0163-3864
VL - 65
SP - 1685
EP - 1689
JO - Journal of Natural Products
JF - Journal of Natural Products
IS - 11
ER -