18O2 labeling experiments illuminate the oxidation of ent-kaurene in bacterial gibberellin biosynthesis,Organic & Biomolecular Chemistry

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18O2 labeling experiments illuminate the oxidation of ent-kaurene in bacterial gibberellin biosynthesis
Organic & Biomolecular Chemistry ( IF 2.9 ) Pub Date : 2017-08-25 00:00:00 , DOI: 10.1039/c7ob01819c
Raimund Nagel _{1,

2,

3,

4,

5} , Reuben J. Peters _{1,

2,

3,

4,

5}

Affiliation

Bacteria can produce gibberellin plant hormones. While the bacterial biosynthetic pathway is similar to that of plants, the individual enzymes are very distantly related and arose via convergent evolution. The cytochromes P450 (CYPs) that catalyze the multi-step oxidation of the alkane precursor ent-kaurene (1) to ent-kauren-19-oic acid (5), are called ent-kaurene oxidases (KOs), and in plants are from the CYP701 family, and share less than 19% amino acid sequence identity with those from bacteria, which are from the phylogenetically distinct CYP117 family. Here the reaction series catalyzed by CYP117 was examined by ¹⁸O₂ labeling experiments, the results indicate successive hydroxylation of 1 to ent-kauren-19-ol (2) and then ent-kauren-19,19-diol (3) and most likely an intervening dehydration to ent-kauren-19-al (4) prior to the concluding hydroxylation to 5. Accordingly, the bacterial and plant KOs converged on catalysis of the same series of reactions, despite their independent evolutionary origin.

中文翻译：

¹⁸ O₂标记实验阐明了细菌赤霉素生物合成过程中ent- Kaurene的氧化

细菌可以产生赤霉素植物激素。尽管细菌的生物合成途径与植物相似，但各个酶之间的关系却非常遥远，并且是通过趋同进化而产生的。催化烷烃前体ent -kaurene（1）到ent -kauren-19-oic acid（5）的多步氧化的细胞色素P450（CYPs）被称为ent -kaurene氧化酶（KOs），在植物中有CYP701家族成员的氨基酸序列与细菌的氨基酸序列同一性少于19％，细菌来自系统发育上独特的CYP117家族。在这里，用¹⁸ O ₂检验了由CYP117催化的反应系列标记实验，结果表明的连续羟化1至ENT -kauren-19醇（2），然后ENT -kauren-19,19二醇（3），最有可能的居间脱水以ENT -kauren-19-AL（4）在结束之前羟化到5。因此，尽管细菌和植物KOs是独立的进化起源，但它们在相同系列反应的催化作用下会聚。

更新日期：2017-09-20

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