THERMOSTABLE ENZYMES IN ORGANIC-SYNTHESIS .6. TOTAL SYNTHESIS OF (S)-(-)-ZEARALENONE USING A TBADH-GENERATED TRIFUNCTIONAL CHIRON
THERMOSTABLE ENZYMES IN ORGANIC-SYNTHESIS .6. TOTAL SYNTHESIS OF (S)-(-)-ZEARALENONE USING A TBADH-GENERATED TRIFUNCTIONAL CHIRON
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DOI：
10.1039/p19910003333
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发表时间：
1991-12-01
期刊：
影响因子：
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通讯作者：
SINHABAGCHI, A
中科院分区：
文献类型：
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作者：
KEINAN, E;SINHA, SC;SINHABAGCHI, A
由热厌氧菌醇脱氢酶 (TBADH) 催化多官能酮的不对称还原产生的手性醇是天然产物合成的有用构建单元。 特别是，通过酶促还原 dec-9-ene-2,6-二酮生成光学纯的 (S)-2-羟基dec-9-en-6-酮，证明了 TBADH 区分具有相同化学反应性的两种酮的能力。 以后者为起始原料，全合成了光学纯度超过99.5%的(S)-(-)-玉米赤霉烯酮。
Chiral alcohols produced by Thermoanaerobium brockii alcohol dehydrogenase (TBADH)-catalysed asymmetric reduction of polyfunctional ketones are useful building blocks for natural products synthesis. In particular, the ability of TBADH to discriminate between two ketones having equal chemical reactivity is demonstrated by enzymatic reduction of dec-9-ene-2,6-dione to produce optically pure (S)-2-hydroxydec-9-en-6-one. The total synthesis of (S)-(-)-zearalenone with optical purity that exceeds 99.5% has been achieved by using the latter compound as a starting material.