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Enzyme and Reaction Engineering in Biocatalysis: Synthesis of (S)-Methoxyisopropylamine (= (S)-1-Methoxypropan-2-amine)
CHIMIA International Journal for Chemistry ( IF 1.1 ) Pub Date : 2022-05-09 , DOI: 10.2533/chimia.1999.584 George Matcham , Mohit Bhatia , Wei Lang , Craig Lewis , Richard Nelson , Alice Wang , Wei Wu
CHIMIA International Journal for Chemistry ( IF 1.1 ) Pub Date : 2022-05-09 , DOI: 10.2533/chimia.1999.584 George Matcham , Mohit Bhatia , Wei Lang , Craig Lewis , Richard Nelson , Alice Wang , Wei Wu
Methoxyisopropylamine is a chiral amine moiety common to the chemical structures of two important chloroacetamide herbicides, metolachlor and dimethenamid. The activity of both products lies predominantly in their (S)-enantiomeric forms. Celgro scientists have developed a high-productivity biocatalytic process to (S)-methoxyisopropylamine via transamination of methoxyacetone and isopropylamine. Biocatalyst and process optimization was achieved by integration of molecular biology, fermentation, enzymology, and engineering disciplines to identify and overcome kinetic, stability, and thermodynamic constraints on productivity. The result was a 50° vacuum reaction producing 2M (S)-methoxyisopropylamine (18 wt-%) at >99% ee, with 97% conversion of methoxyacetone in 7 h, meeting economic targets applicable to agrochemical manufacturing.
中文翻译:
生物催化中的酶与反应工程:(S)-甲氧基异丙胺(= (S)-1-甲氧基丙-2-胺)的合成
甲氧基异丙胺是两种重要的氯乙酰胺除草剂异丙甲草胺和噻吩草胺的化学结构所共有的手性胺部分。两种产品的活性主要在于其 (S)-对映体形式。 Celgro 的科学家们开发出了一种通过甲氧基丙酮和异丙胺的转氨作用生产 (S)-甲氧基异丙胺的高产生物催化工艺。生物催化剂和工艺优化是通过分子生物学、发酵、酶学和工程学科的整合来实现的,以识别和克服对生产力的动力学、稳定性和热力学限制。结果是 50° 真空反应生成 2M (S)-甲氧基异丙胺 (18 wt-%),EE 值 >99%,甲氧基丙酮在 7 小时内转化率为 97%,满足农用化学品制造的经济目标。
更新日期:2022-05-09
中文翻译:
生物催化中的酶与反应工程:(S)-甲氧基异丙胺(= (S)-1-甲氧基丙-2-胺)的合成
甲氧基异丙胺是两种重要的氯乙酰胺除草剂异丙甲草胺和噻吩草胺的化学结构所共有的手性胺部分。两种产品的活性主要在于其 (S)-对映体形式。 Celgro 的科学家们开发出了一种通过甲氧基丙酮和异丙胺的转氨作用生产 (S)-甲氧基异丙胺的高产生物催化工艺。生物催化剂和工艺优化是通过分子生物学、发酵、酶学和工程学科的整合来实现的,以识别和克服对生产力的动力学、稳定性和热力学限制。结果是 50° 真空反应生成 2M (S)-甲氧基异丙胺 (18 wt-%),EE 值 >99%,甲氧基丙酮在 7 小时内转化率为 97%,满足农用化学品制造的经济目标。