Biological Reaction Engineering for the Preparation of C9 Chemicals from Oleic Acid: 9-Aminononanoic Acid, 1,9-Nonanediol, 9-Amino-1-nonanol, and 1,9-Diaminononane,ACS Catalysis

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Biological Reaction Engineering for the Preparation of C9 Chemicals from Oleic Acid: 9-Aminononanoic Acid, 1,9-Nonanediol, 9-Amino-1-nonanol, and 1,9-Diaminononane
ACS Catalysis ( IF 11.3 ) Pub Date : 2024-03-04 , DOI: 10.1021/acscatal.4c00302
Se-Yeun Hwang ₁ , Ji-Min Woo ₁ , Go Eun Choi ₁ , Deok-Kun Oh ₂ , Joo-Hyun Seo ₃ , Jin-Byung Park ₁

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Engineering of native and recombinant enzyme reactions in whole-cell biocatalysis may allow the production of a variety of chemicals. In particular, fine-tuning of the reaction selectivity may enable the preparation of a desired product to a high conversion. Here, we demonstrated that various C9 chemicals such as 9-aminononanoic acid, 1,9-nonanediol, 9-amino-1-nonanol, and 1,9-diaminononane could be produced from renewable C18 oleic acid. As a representative example, activation of six recombinant enzyme reactions (e.g., fatty acid double bond hydratase, long-chain secondary alcohol dehydrogenase, Baeyer–Villiger monooxygenase, lipase, primary alcohol dehydrogenase, and ω-aminotransferases) with repression of one native enzyme reaction (i.e., aldehyde dehydrogenase) in Escherichia coli-based biocatalysis led to the formation of 9-aminononanoic acid with an isolation yield of 54% from oleic acid via 10-hydroxyoctadecanoic acid, 10-keto-octadecanoic acid, 9-(nonanoyloxy)nonanoic acid, 9-hydroxynonanoic acid, and 9-oxo-nonanoic acid. This study will contribute to biosynthesis of not only ω-aminoalkanoic acids but also ω-amino-1-alkanols and α,ω-diaminoalkanes from renewable fatty acids (e.g., oleic acid and ricinoleic acid).

中文翻译：

油酸制备C9化学品的生物反应工程：9-氨基壬酸、1,9-壬二醇、9-氨基-1-壬醇和1,9-二氨基壬烷

全细胞生物催化中天然和重组酶反应的工程可以允许生产多种化学品。特别是，反应选择性的微调可以使所需产物的制备达到高转化率。在这里，我们证明了可以用可再生的 C18 油酸生产各种 C9 化学品，如 9-氨基壬酸、1,9-壬二醇、9-氨基-1-壬醇和 1,9-二氨基壬烷。作为一个代表性的例子，激活六种重组酶反应（例如，脂肪酸双键水合酶、长链仲醇脱氢酶、Baeyer-Villiger单加氧酶、脂肪酶、伯醇脱氢酶和ω-氨基转移酶）并抑制一种天然酶反应大肠杆菌中的醛脱氢酶（即醛脱氢酶）通过 10-羟基十八烷酸、10-酮基十八烷酸、9-(壬酰氧基)壬酸从油酸中形成 9-氨基壬酸，分离产率为 54%酸、9-羟基壬酸和9-氧代-壬酸。这项研究不仅有助于从可再生脂肪酸（例如油酸和蓖麻油酸）生物合成 ω-氨基链烷酸，还有助于生物合成 ω-氨基-1-链烷醇和 α,ω-二氨基烷烃。

更新日期：2024-03-04

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