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      • Biosynthetic Studies on the a-Glucosidase Inhibitor Acarbose and Validamycin A

        Sauerbrei, Bernd,Niggemann, Jutta,Mahmud, Taifo,Dong, Haijun,Tornus, Ingo,Egelkrout, Erin,Wolf, Eckardt,Uy, Charmaine,Lee, Sungsook 선문대학교 첨단과학기술연구소 2001 첨단과학기술연구소 논문집 Vol.5 No.-

        To investigate the source of the maltose unit in acarbose, feeding experiments using ³H- or ²H-labeled maltose or maltotriose were carried out with resting cells of Actinoplanes sp. SN223/29. It was found that acarbose is formed from maltotriose by two routes as shown in Figure 2. It was observed that glutamate is to be the preferred nitrogen source among the tested ^(13)N-labeled compounds, showing the mode of nitrogen introduction is a PI,P-dependent transamination, and ammonium chloride is a good alternative nitrogen source under conditions glutamate shortage. The biosynthetic pathway leading to the mC_(7)N cyclitol (valienamine) moiety of acarbose (l) has been studied using ³H-,²H-,and ^(13)C-labeled cyclitols. The feeding experiments demonstrated that cyclitols having the same stereo chemistry at C-2 as the valienamine moiety of acarbose, i.e., valienone, valienamine, valiolone, valiolamine were not incorporated and thus are not plausible intermediates in l biosynthesis. 2-Epi-valiolone (l0b), which has the same stereochemistry as the presumed open chain precursor, sedoheptulose 7-phosphate was also notincorporated. However, its C-5 epimer (10a) was incorporated efficiently and specifically into the valienamine moiety of l. Surprisingly, the dehydrated form of 2-epi-5-epi-valiolone, 2-epi-valienone, was not incorporated. This suggests that 2-epi-5-epi-valiolone (10a)must be converted directly into the pseudodisaccharide moiety of acarbose without the intervention of other free cyclitol intermediates. However, it was found that not only l0a but also valienone were incorporated into validamycin A (2).

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