Enzymatic synthesis of pharmacologically relevant chiral sulfoxides by improved CbBVMO variants
Literature Information
Publication Date
2023-11-14
DOI
10.1039/D3CC05463B
Impact Factor
6.222
Authors
Chen Zhao, Feng Liu, Min Zhou, Qiang Geng, Hui-Lei Yu
View Original
Abstract
Baeyer–Villiger monooxygenases (BVMOs) are able to catalyse the asymmetric oxidation of sulfides. This property has made them attractive catalysts for the synthesis of chiral sulfoxide drugs. Here, we have designed and synthesised an exhaustive combinatorial mutant library of the previously identified lansoprazole sulfide monooxygenase CbBVMOV1. From this synthetic combinatorial mutant library, the best mutant, CbBVMOV3, was selected with a specific activity of approximately 1 U mg−1 for lansoprazole sulfoxides. We then optimised the reaction conditions of a two-phase system, achieving the enzymatic asymmetric synthesis of (R)-lansoprazole in a space-time yield of 213 g L−1 d−1 and an enantiomeric excess of >99% (R) with no detectable by-products. In addition, CbBVMOV3 showed higher activity towards other prazole sulfides. These results indicate the potential application of CbBVMO in the chiral sulfoxide drug industry.
Related Literature
Mapping the structure of amyloid nucleation precursors by protein engineering kinetic analysis
David Ruzafa, Lorena Varela, Ana I. Azuaga, Francisco Conejero-Lara, Bertrand Morel
2013-12-06
Paper
DOI: 10.1039/C3CP54383H
Ionic liquid modulation of swelling and LCST behavior of N-isopropylacrylamide polymer gels
Simon Gallagher, Andrew Kavanagh, Bartosz Zíołkowski, Larisa Florea, Douglas R. MacFarlane, Kevin Fraser, Dermot Diamond
2013-12-18
Paper
DOI: 10.1039/C3CP53397B
Reply to the ‘Comment on “Volume shrinkage of a metal–organic framework host induced by the dispersive attraction of guest gas molecules”’ by F.-X. Coudert, A. H. Fuchs, and A. V. Neimark, Phys. Chem. Chem. Phys.
Jaeyong Joo, Hyungjun Kim, Sang Soo Han
2014-01-07
Comment
DOI: 10.1039/C3CP54473G
Adsorption studies of a phosphonic acid on ITO: film coverage, purity, and induced electronic structure changes
S. A. Paniagua, E. L. Li, S. R. Marder
2013-12-19
Paper
DOI: 10.1039/C3CP54637C
Electronic and magnetic structures of coronene-based graphitic nanoribbons
Aldilene Saraiva-Souza, Zachary Bullard, Dayvison Weber Maia, Antônio Gomes Souza Filho, Eduardo Costa Girão
2013-12-16
Paper
DOI: 10.1039/C3CP54496F
Experimental and theoretical study on the sensing mechanism of a fluorescence probe for hypochloric acid: a Se⋯N nonbonding interaction modulated twisting process
Songqiu Yang, Peng Li, Panwang Zhou, Keli Han
2013-11-26
Paper
DOI: 10.1039/C3CP54093F
Photoelectrochemical scanning droplet cell microscopy for localized photovoltaic investigations on organic semiconductors
Jacek Gasiorowski, Jan Philipp Kollender, Kurt Hingerl, Niyazi Serdar Sariciftci, Andrei Ionut Mardare
2013-11-18
Paper
DOI: 10.1039/C3CP53851F
Competitive pi interactions and hydrogen bonding within imidazolium ionic liquids
Richard P. Matthews, Tom Welton, Patricia A. Hunt
2014-01-09
Paper
DOI: 10.1039/C3CP54672A
Synthesis and characterization of graphene: influence of synthesis variables
M. P. Lavin-Lopez, J. L. Valverde, M. C. Cuevas, A. Garrido, L. Sanchez-Silva, P. Martinez, A. Romero-Izquierdo
2013-12-04
Paper
DOI: 10.1039/C3CP54832E
Shape selectivity using ionic liquids for the preparation of silver and silver sulphide nanomaterials
Amol B. Patil, Bhalchandra M. Bhanage
2013-12-16
Paper
DOI: 10.1039/C3CP54382J
You might also like
Compound Q&A
What is the market or research trend for N-(4-Methoxybenzyl)-2-pyridinamine (CAS: 52818-63-0)?
N-(4-Methoxybenzyl)-2-pyridinamine (CAS: 52818-63-0) is increasingly being used ...
52818-63-0N-(4-Methoxybenzyl)-...
Compound Q&A
What precautions should be taken when handling Ethyl 4-(2-chlorophenyl)-1,3-thiazole-2-carboxylate (CAS: 1050507-06-6)?
When handling Ethyl 4-(2-chlorophenyl)-1,3-thiazole-2-carboxylate, appropriate p...
1050507-06-6Ethyl 4-(2-chlorophe...
Compound Q&A
What regulatory guidelines apply to diethyldiselane (CAS: 628-39-7)?
Diethyldiselane (CAS: 628-39-7) is classified under the Globally Harmonized Syst...
628-39-7Diethyldiselane
Compound Q&A
What is the market or research trend for oxocopper (CAS: 12053-18-8)?
The market for oxocopper (CAS: 12053-18-8) is primarily driven by its use in cat...
12053-18-8oxocopper; oxo-(oxoc...
Compound Q&A
What is the market or research trend for 5-{[(2-Methyl-2-propanyl)oxy]carbonyl}-5-azaspiro[2.4]heptane-7-carboxylic acid?
The market for 5-{[(2-Methyl-2-propanyl)oxy]carbonyl}-5-azaspiro[2.4]heptane-7-c...
1268519-54-55-{[(2-Methyl-2-prop...
Compound Q&A
What is 2-(1-Pyrrolidinyl)-4-pyridinamine (CAS: 35981-63-6)?
2-(1-Pyrrolidinyl)-4-pyridinamine is a chemical compound with the CAS number 359...
35981-63-62-(1-Pyrrolidinyl)-4...
Compound Q&A
What are the physical and chemical properties of 2-(3-Pyridinyl)-1-azabicyclo[2.2.2]octane (CAS: 91556-75-1)?
2-(3-Pyridinyl)-1-azabicyclo[2.2.2]octane (CAS: 91556-75-1) is a crystalline sol...
91556-75-12-(3-Pyridinyl)-1-az...
Compound Q&A
How is (S)-Alpha-allyl-proline hydrochloride (CAS: 129704-91-2) typically synthesized?
(S)-Alpha-allyl-proline hydrochloride is usually synthesized via a Wittig reacti...
129704-91-2(S)-Alpha-allyl-prol...
Compound Q&A
What is 3-Methyl-1,2-oxazole-5-carboxylic acid (CAS: 4857-42-5)?
3-Methyl-1,2-oxazole-5-carboxylic acid (CAS: 4857-42-5) is an organic compound w...
4857-42-53-Methyl-1,2-oxazole...
Compound Q&A
How is Lys-SMCC-DM1 (CAS: 1281816-04-3) typically synthesized?
Lys-SMCC-DM1 is synthesized via a multi-step process involving the coupling of S...
1281816-04-3Lys-SMCC-DM1
Source Journal
Chemical Communications
CiteScore:
8.6
Self-citation Rate:
4.7%
Articles per Year:
2458
ChemComm publishes urgent research which is of outstanding significance and interest to experts in the field, while also appealing to the journal’s broad chemistry readership. Our communication format is ideally suited to short, urgent studies that are of such importance that they require accelerated publication. Our scope covers all topics in chemistry, and research at the interface of chemistry and other disciplines (such as materials science, nanoscience, physics, engineering and biology) where there is a significant novelty in the chemistry aspects. Major topic areas covered include: Analytical Chemistry Catalysis Chemical Biology and medicinal chemistry Computational Chemistry and Machine Learning Energy and sustainable chemistry Environmental Chemistry Green Chemistry Inorganic Chemistry Materials Chemistry Nanoscience Organic Chemistry Physical Chemistry Polymer Chemistry Supramolecular Chemistry
Recommended Compounds
Benzyl 6-oxo-3,6-dihydro-1(2H)-pyridinecarboxylate
CAS Number:
725746-35-0
Molecular Formula:
C13H13NO3
![1-[6-(1H-Imidazol-1-yl)-3-pyridinyl]methanamine structure](https://static.chemtradehub.com/structs/914/914637-08-4-8825.webp "1-[6-(1H-Imidazol-1-yl)-3-pyridinyl]methanamine structure")
![1-(1-Benzyl-1,2,3,6-tetrahydropyridin-4-yl)-1H-benzo[d]imidazol-2(3H)-one structure](https://static.chemtradehub.com/structs/603/60373-71-9-7dfb.webp "1-(1-Benzyl-1,2,3,6-tetrahydropyridin-4-yl)-1H-benzo[d]imidazol-2(3H)-one structure")
1-(1-Benzyl-1,2,3,6-tetrahydropyridin-4-yl)-1H-benzo[d]imidazol-2(3H)-one
CAS Number:
60373-71-9
Molecular Formula:
C19H19N3O
![1-oxaspiro[4.4]nonan-6-one structure](https://static.chemtradehub.com/structs/134/134179-01-4-e051.webp "1-oxaspiro[4.4]nonan-6-one structure")
Recommended Suppliers
Disclaimer
This page provides academic journal information for reference and research purposes only. We are not affiliated with any journal publishers and do not handle publication submissions. For publication-related inquiries, please contact the respective journal publishers directly.
If you notice any inaccuracies in the information displayed, please contact us at support@chemtradehub.com. We will promptly review and address your concerns.