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Selective hydroxylation of highly branched fatty acids and their derivatives by CYP102A1 from Bacillus megaterium

机译：通过来自巨大芽孢杆菌的CYp102a1选择性羟基化高度支化的脂肪酸及其衍生物

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Highly branched fatty acids, representing the main component of the preen gland wax of the domestic goose, and their derivatives are promising chiral precursors for the synthesis of macrolid antibiotics. The key step in utilisation of these compounds is the regioselective hydroxylation, which can not be done in a classical chemical approach.Three P450 monooxygenases CYP102A1, CYP102A2 and CYP102A3, demonstrating high turnover numbers in hydroxylation of iso and anteiso fatty acids (>400 min-1), were tested for their activity towards these substrates. CYP102A1 from Bacillus megaterium as well as its A74G F87V L188Q triple mutant hydroxylate a variety of these substrates with high activity and regioselectivity. In all cases the triple mutant showed much higher activities than the wild type enzyme. The binding constants, determined for CYP102A1 wild type and the triple mutant were >200 µM and ~23 µM, respectively, when tetramethyl nonanol was used as substrate. The data derived from binding analysis supports the differences in activity found for the CYP102A1 wild type and the triple mutant.Surprisingly the CYP102A2 and CYP102A3 from Bacillus subtilis did not show activity at all. Substrate binding spectra, recorded to investigate substrate accessibility to the enzyme’s active site, revealed that the substrates either could not access the active site of the Bacillus subtilis monooxygenases, or did not reach the heme proximity.
机译：高度支化的脂肪酸代表了家鹅的唇腺蜡的主要成分，它们的衍生物是合成大环内酯抗生素的有希望的手性前体。利用这些化合物的关键步骤是区域选择性羟基化，这是经典化学方法无法实现的。三种P450单加氧酶CYP102A1，CYP102A2和CYP102A3，证明异和前异脂肪酸的羟基化反应具有较高的转换率（> 400 min- 1），测试它们对这些底物的活性。来自巨大芽孢杆菌的CYP102A1及其A74G F87V L188Q三重突变体羟基化了这些具有高活性和区域选择性的各种底物。在所有情况下，三重突变体均显示出比野生型酶高得多的活性。当以四甲基壬醇为底物时，测定的CYP102A1野生型和三重突变体的结合常数分别为> 200 µM和〜23 µM。结合分析得出的数据支持CYP102A1野生型和三重突变体活性的差异。令人惊讶的是，来自枯草芽孢杆菌的CYP102A2和CYP102A3根本没有显示活性。记录底物结合光谱以调查底物对酶活性位点的可及性，结果表明底物要么不能接近枯草芽孢杆菌单加氧酶的活性位点，要么无法达到血红素的亲和力。

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