Parallel anti-sense two-step cascade for alcohol amination leading to ω-amino fatty acids and α,ω-diamines,Green Chemistry

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Parallel anti-sense two-step cascade for alcohol amination leading to ω-amino fatty acids and α,ω-diamines
Green Chemistry ( IF 9.3 ) Pub Date : 2018-09-26 , DOI: 10.1039/c8gc02122h
Sihyong Sung _{1,

2,

3,

4} , Hyunwoo Jeon _{1,

2,

3,

4} , Sharad Sarak _{1,

2,

3,

4} , Md Murshidul Ahsan _{4,

5,

6,

7} , Mahesh D. Patil _{1,

2,

3,

4} , Wolfgang Kroutil _{8,

9,

10,

11} , Byung-Gee Kim _{4,

12,

13,

14} , Hyungdon Yun _{1,

2,

3,

4}

Affiliation

Running two two-step cascades in parallel anti-sense to transform an alcohol to an amine allowed the conversion of ω-hydroxy fatty acids (ω-HFAs) and α,ω-diols to the corresponding ω-amino fatty acids (ω-AmFAs) and α,ω-diamines, respectively. The network required only two enzymes namely an aldehyde reductase (AHR) and a transaminase (TA). Benzylamine served on the one hand as amine donor and on the other hand after deamination to benzaldehyde also as oxidant. All ω-HFAs tested were efficiently transformed to their corresponding ω-AmFAs using purified enzymes as well as a whole-cell system, separately expressing both the enzymes, with conversions ranging from 80–95%. Additionally, a single-cell co-expressing all enzymes successfully produced the ω-AmFAs as well as the α,ω-diamines with >90% yield. This system was extended by employing a lactonase, enabling the transformation of ε-caprolactone to its corresponding ω-AmFA with >80% conversion.

中文翻译：

平行反义两步级联用于醇胺化反应，生成ω-氨基酸脂肪酸和α，ω-二胺

将两个两步式级联反应平行进行反义以将醇转化为胺，可将ω-羟基脂肪酸（ω-HFA）和α，ω-二醇转化为相应的ω-氨基酸脂肪酸（ω-AmFAs））和α，ω-二胺。该网络仅需要两种酶，即醛还原酶（AHR）和转氨酶（TA）。苄胺一方面用作胺供体，另一方面在脱氨基后生成苯甲醛也用作氧化剂。使用纯化的酶以及全细胞系统将所有测试的ω-HFA有效地转化为其相应的ω-AmFA，分别表达两种酶，转化率在80-95％之间。另外，单细胞共表达所有酶均成功产生了ω-AmFA和α，ω-二胺，产率> 90％。

更新日期：2018-10-15

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