Hydrogen Bonds and n → π* Interactions in the Acetylation of Propranolol Catalyzed by Candida antarctica Lipase B: A QTAIM Study
Enzyme–substrate interactions play a crucial role in enzymatic catalysis. Quantum theory of atoms in molecules (QTAIM) calculations are extremely useful in computational studies of these interactions because they provide very detailed information about the strengths and types of molecular interactio...
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ftsmithonian:oai:figshare.com:article/15101719 2023-05-15T13:56:27+02:00 Hydrogen Bonds and n → π* Interactions in the Acetylation of Propranolol Catalyzed by Candida antarctica Lipase B: A QTAIM Study David A. Rincón (11226802) Markus Doerr (1441585) Martha C. Daza (3369596) 1753-01-01T00:00:00Z https://doi.org/10.1021/acsomega.1c02559.s002 unknown https://figshare.com/articles/dataset/Hydrogen_Bonds_and_n__Interactions_in_the_Acetylation_of_Propranolol_Catalyzed_by_Candida_antarctica_Lipase_B_A_QTAIM_Study/15101719 doi:10.1021/acsomega.1c02559.s002 CC BY-NC 4.0 CC-BY-NC Biophysics Biochemistry Pharmacology Biotechnology Marine Biology Computational Biology Chemical Sciences not elsewhere classified electron density Candida antarctica lipase B D 187 acts electron density reservoir H 224 acts enantioselective step Hydrogen Bonds covalent hydrogen bonds interaction intramolecular changes reaction paths NBO Propranolol Catalyzed quantum theory releases electron density oxyanion hole QTAIM topological properties Dataset 1753 ftsmithonian https://doi.org/10.1021/acsomega.1c02559.s002 2021-12-20T05:07:00Z Enzyme–substrate interactions play a crucial role in enzymatic catalysis. Quantum theory of atoms in molecules (QTAIM) calculations are extremely useful in computational studies of these interactions because they provide very detailed information about the strengths and types of molecular interactions. QTAIM also provides information about the intramolecular changes that occur in the catalytic reaction. Here, we analyze the enzyme–substrate interactions and the topological properties of the electron density in the enantioselective step of the acylation of ( R , S )-propranolol, an aminoalcohol with therapeutic applications, catalyzed by Candida antarctica lipase B. Eight reaction paths (four for each enantiomer) are investigated and the energies, atomic charges, hydrogen bonds, and n → π* interactions of propranolol, the catalytic triad (composed of D187, H224, and S105), and the oxyanion hole are analyzed. It is found that D187 acts as an electron density reservoir for H224, and H224 acts as an electron density reservoir for the active site of the protein. It releases electron density when the tetrahedral intermediate is formed from the Michaelis complex and receives it when the enzyme–product complex is formed. Hydrogen bonds can be grouped into noncovalent and covalent hydrogen bonds. The latter are stronger and more important for the reaction than the former. We also found weak n → π* interactions, which are characterized by QTAIM and the natural bond orbital (NBO) analysis. Dataset Antarc* Antarctica Unknown |
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op_collection_id |
ftsmithonian |
language |
unknown |
topic |
Biophysics Biochemistry Pharmacology Biotechnology Marine Biology Computational Biology Chemical Sciences not elsewhere classified electron density Candida antarctica lipase B D 187 acts electron density reservoir H 224 acts enantioselective step Hydrogen Bonds covalent hydrogen bonds interaction intramolecular changes reaction paths NBO Propranolol Catalyzed quantum theory releases electron density oxyanion hole QTAIM topological properties |
spellingShingle |
Biophysics Biochemistry Pharmacology Biotechnology Marine Biology Computational Biology Chemical Sciences not elsewhere classified electron density Candida antarctica lipase B D 187 acts electron density reservoir H 224 acts enantioselective step Hydrogen Bonds covalent hydrogen bonds interaction intramolecular changes reaction paths NBO Propranolol Catalyzed quantum theory releases electron density oxyanion hole QTAIM topological properties David A. Rincón (11226802) Markus Doerr (1441585) Martha C. Daza (3369596) Hydrogen Bonds and n → π* Interactions in the Acetylation of Propranolol Catalyzed by Candida antarctica Lipase B: A QTAIM Study |
topic_facet |
Biophysics Biochemistry Pharmacology Biotechnology Marine Biology Computational Biology Chemical Sciences not elsewhere classified electron density Candida antarctica lipase B D 187 acts electron density reservoir H 224 acts enantioselective step Hydrogen Bonds covalent hydrogen bonds interaction intramolecular changes reaction paths NBO Propranolol Catalyzed quantum theory releases electron density oxyanion hole QTAIM topological properties |
description |
Enzyme–substrate interactions play a crucial role in enzymatic catalysis. Quantum theory of atoms in molecules (QTAIM) calculations are extremely useful in computational studies of these interactions because they provide very detailed information about the strengths and types of molecular interactions. QTAIM also provides information about the intramolecular changes that occur in the catalytic reaction. Here, we analyze the enzyme–substrate interactions and the topological properties of the electron density in the enantioselective step of the acylation of ( R , S )-propranolol, an aminoalcohol with therapeutic applications, catalyzed by Candida antarctica lipase B. Eight reaction paths (four for each enantiomer) are investigated and the energies, atomic charges, hydrogen bonds, and n → π* interactions of propranolol, the catalytic triad (composed of D187, H224, and S105), and the oxyanion hole are analyzed. It is found that D187 acts as an electron density reservoir for H224, and H224 acts as an electron density reservoir for the active site of the protein. It releases electron density when the tetrahedral intermediate is formed from the Michaelis complex and receives it when the enzyme–product complex is formed. Hydrogen bonds can be grouped into noncovalent and covalent hydrogen bonds. The latter are stronger and more important for the reaction than the former. We also found weak n → π* interactions, which are characterized by QTAIM and the natural bond orbital (NBO) analysis. |
format |
Dataset |
author |
David A. Rincón (11226802) Markus Doerr (1441585) Martha C. Daza (3369596) |
author_facet |
David A. Rincón (11226802) Markus Doerr (1441585) Martha C. Daza (3369596) |
author_sort |
David A. Rincón (11226802) |
title |
Hydrogen Bonds and n → π* Interactions in the Acetylation of Propranolol Catalyzed by Candida antarctica Lipase B: A QTAIM Study |
title_short |
Hydrogen Bonds and n → π* Interactions in the Acetylation of Propranolol Catalyzed by Candida antarctica Lipase B: A QTAIM Study |
title_full |
Hydrogen Bonds and n → π* Interactions in the Acetylation of Propranolol Catalyzed by Candida antarctica Lipase B: A QTAIM Study |
title_fullStr |
Hydrogen Bonds and n → π* Interactions in the Acetylation of Propranolol Catalyzed by Candida antarctica Lipase B: A QTAIM Study |
title_full_unstemmed |
Hydrogen Bonds and n → π* Interactions in the Acetylation of Propranolol Catalyzed by Candida antarctica Lipase B: A QTAIM Study |
title_sort |
hydrogen bonds and n → π* interactions in the acetylation of propranolol catalyzed by candida antarctica lipase b: a qtaim study |
publishDate |
1753 |
url |
https://doi.org/10.1021/acsomega.1c02559.s002 |
genre |
Antarc* Antarctica |
genre_facet |
Antarc* Antarctica |
op_relation |
https://figshare.com/articles/dataset/Hydrogen_Bonds_and_n__Interactions_in_the_Acetylation_of_Propranolol_Catalyzed_by_Candida_antarctica_Lipase_B_A_QTAIM_Study/15101719 doi:10.1021/acsomega.1c02559.s002 |
op_rights |
CC BY-NC 4.0 |
op_rightsnorm |
CC-BY-NC |
op_doi |
https://doi.org/10.1021/acsomega.1c02559.s002 |
_version_ |
1766263960938479616 |