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Interrogating chemical mechanisms in natural products biosynthesis using quantum chemical calculations
Author(s) -
Tantillo Dean J.
Publication year - 2019
Publication title -
wiley interdisciplinary reviews: computational molecular science
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 5.126
H-Index - 81
eISSN - 1759-0884
pISSN - 1759-0876
DOI - 10.1002/wcms.1453
Subject(s) - pericyclic reaction , carbocation , chemistry , natural product , mechanism (biology) , biochemical engineering , reactivity (psychology) , computational chemistry , reaction mechanism , quantum chemical , chemical reaction , chemical biology , catalysis , molecule , stereochemistry , organic chemistry , biochemistry , epistemology , philosophy , medicine , engineering , alternative medicine , pathology
Quantum chemical methods are useful for probing the energetic viability of chemical mechanisms involved in natural product biosynthesis. Typical computational approaches are described and representative examples of mechanistic studies on radical, pericyclic, and carbocation rearrangement reactions that lead to polycyclic skeletons of complex natural products showcase the utility of such methods in providing understanding and shaping future experimental studies. The importance of inherent substrate reactivity is highlighted and cautions for interpreting computational results are discussed. This article is categorized under: Structure and Mechanism > Reaction Mechanisms and Catalysis Theoretical and Physical Chemistry > Reaction Dynamics and Kinetics Structure and Mechanism > Computational Biochemistry and Biophysics