The role of Pseudomonas cepacia lipase in the asymmetric synthesis of heterocyclic based compounds

Ziarani, Ghodsi Mohammadi; Gholamzadeh, Parisa; Asadiatouei, Paria; Lashgari, Negar

doi:10.1016/j.molcatb.2015.08.022

Cited by 12 publications

(6 citation statements)

References 104 publications

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“…This property has been used to obtain molecules with biological activity. In particular, in the resolution of racemic mixtures to obtain the final product ( Scheme 4 ) [ 137 ] as for APIs resolution ( Scheme 5 and Scheme 6 ) [ 137 , 138 ].…”

Section: Microbial Lipases: Structure and Functionmentioning

confidence: 99%

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Microbial Lipases and Their Potential in the Production of Pharmaceutical Building Blocks

Godoy

Pardo‐Tamayo

Barbosa

2022

IJMS

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Processes involving lipases in obtaining active pharmaceutical ingredients (APIs) are crucial to increase the sustainability of the industry. Despite their lower production cost, microbial lipases are striking for their versatile catalyzing reactions beyond their physiological role. In the context of taking advantage of microbial lipases in reactions for the synthesis of API building blocks, this review focuses on: (i) the structural origins of the catalytic properties of microbial lipases, including the results of techniques such as single particle monitoring (SPT) and the description of its selectivity beyond the Kazlauskas rule as the “Mirror-Image Packing” or the “Key Region(s) rule influencing enantioselectivity” (KRIE); (ii) immobilization methods given the conferred operative advantages in industrial applications and their modulating capacity of lipase properties; and (iii) a comprehensive description of microbial lipases use as a conventional or promiscuous catalyst in key reactions in the organic synthesis (Knoevenagel condensation, Morita–Baylis–Hillman (MBH) reactions, Markovnikov additions, Baeyer–Villiger oxidation, racemization, among others). Finally, this review will also focus on a research perspective necessary to increase microbial lipases application development towards a greener industry.

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Section: Microbial Lipases: Structure and Functionmentioning

confidence: 99%

“… Acetylation towards the resolution of the racemic mixture of 3-hydroxy-2,3-dihydropyrrolo[2,1-b]quinazolin-9(1H)-one using PS lipase (Pseudomonas cepacia lipase) to obtain Vasicinone (molecule with bronchodilator activity and antianaphylactic action) [ 137 ]. …”

Section: Figures Schemes and Tablesmentioning

confidence: 99%

Microbial Lipases and Their Potential in the Production of Pharmaceutical Building Blocks

Godoy

Pardo‐Tamayo

Barbosa

2022

IJMS

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“…With this in mind, in this work, the synthesis of ethyl-oleate, which is a model system [16] , [17] , was investigated using lipases. Lipases are one of the most important enzymes in biocatalysis [18] , since they can be used in a wide range of industrial applications: modification of oils and fats, synthesis of organic compounds [19] , supplements and detergents [20] , in analytical procedures [21] , foods and pharmaceutical processing [22] , [23] , and in the production of biofuels (transesterification and/or esterification processes) [24] .…”

Section: Introductionmentioning

confidence: 99%

Immobilization of CALB on activated chitosan: Application to enzymatic synthesis in supercritical and near-critical carbon dioxide

Santos

Bonazza

Matos

et al. 2017

Biotechnology Reports

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“…PS lipase is known for its high enantioselectivity in asymmetric synthesis . For example Ziarani et al reported high yields and enantiomeric excess for a large array of syntheses, such as S ‐enantioselective esterification of racemic bromoalcohol present on heterocycles . The catalytic activity of immobilized PS lipase in esterification reactions has recently been enhanced by sonication, and combining high activity, reusability and very mild reaction conditions renders this emerging type of chemistry attractive for larger‐scale applications.…”

Section: Lipases Used In Chemoenzymatic Transformationsmentioning

confidence: 99%

“…PF lipase has been used especially in ring‐opening polymerizations, and for instance Kobayashi group reported high conversions in the polymerization of δ‐valerolactone using non‐immobilized PF lipase . PF lipase also showed high activity in the copolymerization of lactones and divinyl esters and glycols, where both eROP and polycondensation took place simultaneously in one‐pot reactions …”

Section: Lipases Used In Chemoenzymatic Transformationsmentioning

confidence: 99%

Recent Developments and Optimization of Lipase-Catalyzed Lactone Formation and Ring-Opening Polymerization

Champagne

Strandman

Zhu

2016

Macromol. Rapid Commun.

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To obtain materials useful for the biomedical field, toxic catalysts should be removed from the synthetic route of polymerization reactions and of their precursors. Lipase-catalyzed ring-opening polymerization and the synthesis of cyclic precursors can be performed with the same catalyst under different conditions. Here, we highlight the use of lipases as catalysts and optimization of their performance for both ring-closing and ring-opening polymerization, via varying parameters such as ring size, concentration, substrate molar ratio, temperature, and solvent. While the conditions for ring-closing reactions and ring-opening polymerizations of small molecules, such as ε-caprolactone, have been extensively explored using Candida antarctica lipase B (CALB), the optimization of macrocyclization, especially for more bulky substrates is surveyed here. Finally, recent methods and polymer architectures are summarized with an emphasis on new procedures for more sustainable chemistry, such as the use of ionic liquids as solvents and recycling of polyesters by enzymatic pathways.

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The role of Pseudomonas cepacia lipase in the asymmetric synthesis of heterocyclic based compounds

Cited by 12 publications

References 104 publications

Microbial Lipases and Their Potential in the Production of Pharmaceutical Building Blocks

Microbial Lipases and Their Potential in the Production of Pharmaceutical Building Blocks

Immobilization of CALB on activated chitosan: Application to enzymatic synthesis in supercritical and near-critical carbon dioxide

Recent Developments and Optimization of Lipase-Catalyzed Lactone Formation and Ring-Opening Polymerization

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