Digitoxosyltetracenomycin C and glucosyltetracenomycin C, two novel elloramycin analogues obtained by exploring the sugar donor substrate specificity of glycosyltransferase ElmGT
Digitoxosyltetracenomycin C and glucosyltetracenomycin C, two novel elloramycin analogues obtained by exploring the sugar donor substrate specificity of glycosyltransferase ElmGT
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DOI：
10.1021/np020112z
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发表时间：
2002-11-01
影响因子：
5.1
通讯作者：
Rohr, J
中科院分区：
文献类型：
--
作者：
Fischer, C;Rodríguez, L;Rohr, J
我们对来自橄榄链霉菌Tu 2353的糖基转移酶ElmGT的探索被扩展到各种以前未探索的糖共底物。研究表明，ElmGT通常将L鼠李糖转移到8-去甲基四环素C，这是合成埃罗霉素的关键步骤，但它也能够处理活化的非脱氧糖-D-葡萄糖和NDP-L-洋地黄二糖，这是ElmGT的NDP-L-糖共底物具有轴向3-OH基团的第一例。所得化合物8-去甲基-8-L-洋地黄四环素C(4)和8-去甲基-8-D-葡萄糖基四环菌素C(7)的结构主要通过H-1和C-13核磁共振谱和质谱学确证。
Our explorations of glycosyltransferase ElmGT from Streptomyces olivaceus Tu 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 H-1 and C-13 NMR spectroscopy and by mass spectrometry.