Identification and Implementation of Biocatalytic Transformations in Route Discovery: Synthesis of Chiral 1,3-Substituted Cyclohexanone Building Blocks,Organic Process Research & Development

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Identification and Implementation of Biocatalytic Transformations in Route Discovery: Synthesis of Chiral 1,3-Substituted Cyclohexanone Building Blocks
Organic Process Research & Development ( IF 3.1 ) Pub Date : 2018-06-22 00:00:00 , DOI: 10.1021/acs.oprd.8b00139
Timin Hadi ₁ , Alba Dı́az-Rodrı́guez ₂ , Diluar Khan ₂ , James P. Morrison ₁ , Justin M. Kaplan ₃ , Kathleen T. Gallagher ₁ , Markus Schober ₄ , Michael R. Webb ₂ , Kristin K. Brown ₅ , Douglas Fuerst ₁ , Radka Snajdrova ₂ , Gheorghe-Doru Roiban ₄

Affiliation

Several biocatalytic approaches for the preparation of optically pure methyl 3-oxocyclohexanecarboxylates (S)-, (R)-1 and 3-oxocyclohexanecarbonitriles (S)-, (R)-2 have been successfully demonstrated. Screening of reaction-focused enzyme collections was used to identify initial hits using three enzymatic strategies. Reaction optimization and scale-up enabled the production of chiral intermediates for route scouting efforts on scales of up to 100 g. The enzymes applied in these processes (lipases, enoate reductases, and nitrilases) have been shown to be robust catalysts for drug manufacturing and represent a green alternative to conventional methods to access these chiral cyclohexanone building blocks.

中文翻译：

路线发现中生物催化转化的鉴定和实施：手性1,3-取代的环己酮结构单元的合成

几个生物催化方法用于制备光学纯的3- oxocyclohexanecarboxylates的（小号） - ，（- [R ）- 1和3- oxocyclohexanecarbonitriles（小号） - ，（- [R ） - 2已经被成功证明。以反应为重点的酶集合的筛选被用于使用三种酶促策略来鉴定初始命中。反应的优化和扩大规模使手性中间体的生产得以进行，规模高达100 g。在这些过程中应用的酶（脂肪酶，烯酸还原酶和腈水解酶）已被证明是用于药物生产的强力催化剂，是访问这些手性环己酮结构单元的常规方法的绿色替代品。

更新日期：2018-06-22

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