Abe Ikuro, Takahashi Yusuke, Lou Weiwei, Noguchi Hiroshi
University of Shizuoka, School of Pharmaceutical Sciences, and The 21st Century COE Program, 52-1 Yada, Shizuoka 422-8526, Japan.
Org Lett. 2003 Apr 17;5(8):1277-80. doi: 10.1021/ol0300165.
[reaction: see text] In the chalcone synthase (CHS) enzyme reaction, both the starter molecule and the extension unit of the polyketide chain elongation reaction were simultaneously replaced with nonphysiological substrates. When incubated with benzoyl-CoA and methylmalonyl-CoA as substrates, recombinant CHS from Scutellaria baicalensis afforded an unnatural novel triketide, 4-hydroxy-3,5-dimethyl-6-phenyl-pyran-2-one, along with a tetraketide, 4-hydroxy-3,5-dimethyl-6-(1-methyl-2-oxo-2-phenyl-ethyl)-pyran-2-one. On the other hand, the enzyme also accepted hexanoyl-CoA and methylmalonyl-CoA as substrates to produce an unnatural novel triketide, 4-hydroxy-3,5-dimethyl-6-pentyl-pyran-2-one.
[反应：见正文] 在查尔酮合酶（CHS）酶反应中，聚酮链延伸反应的起始分子和延伸单元同时被非生理性底物取代。当以苯甲酰辅酶A和甲基丙二酰辅酶A作为底物进行孵育时，黄芩的重组CHS产生了一种非天然的新型三酮化合物，4-羟基-3,5-二甲基-6-苯基-吡喃-2-酮，以及一种四酮化合物，4-羟基-3,5-二甲基-6-(1-甲基-2-氧代-2-苯基-乙基)-吡喃-2-酮。另一方面，该酶也接受己酰辅酶A和甲基丙二酰辅酶A作为底物来产生一种非天然的新型三酮化合物，4-羟基-3,5-二甲基-6-戊基-吡喃-2-酮。
