Abstract

Background: Understanding the enantioselectivity is critical for the assessment of environmental behavior and toxicological effect, as well as the ecological risk. As chirality is an important consideration in green chemistry, recent studies demonstrated that enantioselectivity of typical chiral organic pollutants, especially for chiral pesticides, exists in most processes such as aquatic toxicity and degradation. However, to further clarify the metabolism mechanism of enantioselectivity, especially when catalyzed by cytochrome P450 enzymes, development of computational methods is of great importance in this field.

Methods: In this article, we reviewed many outstanding achievements around the hot field and prosperous direction for the development of chiral compounds in computational analysis. A promising combination of theoretical methods, named hybrid quantum mechanical– molecular mechanics (QM/MM), will potentially make a significant contribution to metabolism mechanism of enantioselectivity by P450s.

Results: The main body was divided into two parts, we first clarified the enantioselectivity of chiral pollutants and environmental safety with twenty-two studies, and the remaining (twenty-one) were about cytochromes P450-mediated metabolism of typical chiral compounds. Furthermore, we enumerated a series of theoretical method for cytochromes P450-mediated metabolism with sixteen essays. This review illustrates the importance of the enantioselective in environmental safety, and then discussed the enantioselectivity of interactions mechanism with cytochromes P450 metabolic. Finally theoretical calculations became available and enabled various hypotheses to be tested and new solutions to be offered, especially for QM/MM methods.

Conclusion: The review emphasized importance of the enantioselectivity of typical chiral organic pollutants exists in many biological processes (such as toxicity and environmental degradation), and discusses the development of computational methods to clarify the mechanism of enantioselectivie metabolism of chiral pollutants which catalyzed by cytochrome P450 enzymes.

Keywords: Chiral pesticide, enantioselectivity, P450s, theoretical method, QM/MM.

Graphical Abstract