α-Oxidative decarboxylation of fatty acids catalysed by cytochrome P450 peroxygenases yielding shorter-alkyl-chain fatty acids†,Catalysis Science & Technology

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α-Oxidative decarboxylation of fatty acids catalysed by cytochrome P450 peroxygenases yielding shorter-alkyl-chain fatty acids†
Catalysis Science & Technology ( IF 4.4 ) Pub Date : 2017-11-24 00:00:00 , DOI: 10.1039/c7cy02263h
Hiroki Onoda _{1,

2,

3,

4} , Osami Shoji _{1,

2,

3,

4,

5} , Kazuto Suzuki _{1,

2,

3,

4} , Hiroshi Sugimoto _{4,

5,

6,

7,

8} , Yoshitsugu Shiro _{4,

9,

10,

11} , Yoshihito Watanabe _{2,

3,

4,

12}

Affiliation

Cytochrome P450 peroxygenases belonging to the CYP152 family catalyse the oxidation of fatty acids using H₂O₂. CYP152N1 isolated from Exiguobacterium sp. AT1b exclusively catalyses the α-selective hydroxylation of myristic acid at physiological H₂O₂ concentration. However, a series of shorter-alkyl-chain fatty acids such as tridecanoic acid were produced from myristic acid by increasing the concentration of H₂O₂ (1–10 mM). The yield of tridecanoic acid from myristic acid reached 17%. An ¹⁸O-labeled oxidant study suggested that CYP152N1 catalysed the overoxidation of α-hydroxymyristic acid to form α-ketomyristic acid, which in turn was spontaneously decomposed by H₂O₂ to yield tridecanoic acid. Crystal structure analysis of CYP152N1 revealed its high similarity to other CYP152 family enzymes, such as CYP152A1 and CYP152B1. MD simulations of α-hydroxymyristic acid accommodated in CYP152N1 proposed a possible pre-oxidation conformation of α-hydroxymyristic acid for the decarboxylation reaction.

中文翻译：

由细胞色素P450过氧化酶催化的脂肪酸的α-氧化脱羧反应，产生较短的烷基链脂肪酸†

属于CYP152家族的细胞色素P450过氧化酶使用H ₂ O ₂催化脂肪酸的氧化。CYP152N1从隔离微小杆菌属菌。AT1b在生理H ₂ O ₂浓度下专门催化肉豆蔻酸的α-选择性羟基化。但是，通过增加H ₂ O ₂（1-10 mM）的浓度，由肉豆蔻酸产生了一系列短链烷基脂肪酸，例如十三烷酸。由肉豆蔻酸得到的十三烷酸的收率达到17％。一个¹⁸O标记的氧化剂研究表明CYP152N1催化α-羟基肉豆蔻酸的过氧化反应形成α-酮麦芽酸，然后H ₂ O ₂自发分解生成十三烷酸。CYP152N1的晶体结构分析显示，它与其他CYP152家族酶（例如CYP152A1和CYP152B1）具有高度相似性。CYP152N1中容纳的α-羟基肉豆蔻酸的MD模拟提出了α-羟基肉豆蔻酸可能用于脱羧反应的预氧化构象。

更新日期：2017-11-24

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