Abstract
Motivation: α-Tocopherol is a molecule obtained primarily from plant sources that are important for the pharmaceutical and cosmetics industry. However, this component has some limitations such as sensitivity to oxygen, presence of light, and high temperatures. For this molecule to become more widely used, it is important to carry out a structural modification so that there is better stability and thus it can carry out its activities. To carry out this structural modification, some modifications are carried out, including the application of biotransformation using enzymes as biocatalysts. Thus, the application of a computational tool that helps in understanding the transport mechanisms of molecules in the tunnels present in the enzymatic structures is of fundamental importance because it promotes a computational screening facilitating bench applications. Objective: The aim of this work was to perform a computational analysis of the biotransformation of α-tocopherol into tocopherol esters, observing the tunnels present in the enzymatic structures as well as the energies which correspond to the transport of molecules. Method: To carry out this work, 9 lipases from different organisms were selected; their structures were analyzed by identifying the tunnels (quantity, conformation, and possibility of transport) and later the calculations of substrate transport for the biotransformation reaction in the identified tunnels were carried out. Additionally, the transport of the product obtained in the reaction through the tunnels was also carried out. Results: In this work, the quantity of existing tunnels in the morphological conformational characteristics in the lipases was verified. Thus, the enzymes with fewer tunnels were RML (3 tunnels), LBC and RNL (4 tunnels), PBLL (5 tunnels), CALB (6 tunnels), HLG (7 tunnels), and LCR and LTL (8 tunnels) and followed by the enzyme LPP with the largest number of tunnels (39 tunnels). However, the enzyme that was most likely to transport substrates in terms of α-tocopherol biotransformation (in relation to the Emax and Ea energies of ligands and products) was CALB, as it obtains conformational and transport characteristics of molecules with a particularity. The most conditions of transport analysis were α-tocopherol tunnel 3 (Emax: −4.6 kcal/mol; Ea: 1.1 kcal/mol), vinyl acetate tunnel 1 (Emax: −2.4 kcal/mol; Ea: 0.1 kcal/mol), and tocopherol acetate tunnel 2 (Emax: −3.7 kcal/mol; Ea: 2 kcal/mol).
Highlights
Better known as vitamin E, α-tocopherol was discovered in 1922; it is a molecule with a fat-soluble characteristic that can be extracted from different plant sources and has great importance for the body’s physiological functions acting on oxidative stress, age, inflammatory diseases, and cardiovascular diseases as well as neurodegenerative diseases (Bartolini et al, 2021)
This information is important to molecular dynamics, as it demonstrates the possibility of observing which pathway is most likely to enter the ligand to pass through the lipase structure and reach the active site to carry out the reaction of interest as well as demonstrate along the way that the binder can go through each tunnel
Through the computational screening performed in this work, it can be verified that the number of existing tunnels in the enzymatic structure does not imply a better biocatalytic result, since the lipase with the largest number of tunnels submitted to in silico analysis in this work was the porcine pancreas lipase (LPP) with 39 tunnels, and no significant results were obtained
Summary
Better known as vitamin E, α-tocopherol was discovered in 1922; it is a molecule with a fat-soluble characteristic that can be extracted from different plant sources and has great importance for the body’s physiological functions acting on oxidative stress, age, inflammatory diseases, and cardiovascular diseases as well as neurodegenerative diseases (Bartolini et al, 2021). The topical use, in addition to carrying out the antioxidant action, it slows down the degradation process of collagen existing in the skin, to protect against ultraviolet rays, which suggests a wide use in antiaging and sun protection products (Abla and Banga, 2014). To obtain these esters, the industry uses chemical routes to obtain the final product
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