In Situ Evaluation of Lipase Performances Through Dynamic Asymmetric Cyanohydrin Resolution

Sakulsombat, Morakot; Vongvilai, Pornrapee; Ramström, Olof

doi:10.1039/c0ob00759e

Cited by 17 publications

(23 citation statements)

References 56 publications

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“…The nitroaldol reaction is one of the first C-C bond-forming reactions used for complex dynamic systems, and its reversibility has been confirmed under basic conditions. 6,19 Hemithioacetal formation has also been utilized in both aqueous and organic solvents, 9,20,21 leading to the rapid formation of virtual dynamic systems in water, whereas base catalyzed real dynamic systems can be produced in organic solvents. Due to the discrete properties of each of the two reaction types, the equilibration features were first addressed.…”

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confidence: 99%

Double parallel dynamic resolution through lipase-catalyzed asymmetric transformation

Zhang

Ramström

2013

Chem. Commun.

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Dynamic systems based on double parallel reactions have been generated and resolved in situ by secondary lipase-catalyzed asymmetric transformation, resulting in high chemo-and enantioselectivities.Over the last few decades, along with the powerful impact of supramolecular chemistry, the pursuit to understand the complexity of life has gained increasing momentum within the scientific community. Living systems noticeably depend on intricate networks of molecular reactions and interactions under both thermodynamic and kinetic control, operating in response to various signals and factors. Some of these features can be addressed using the concept of dynamic chemistry. Derived from the feature of reversibility, dynamic chemistry has been established as a useful methodology for generating and studying complex networks on a molecular scale. At the constitutional level, this has led to molecular networks that enable selection and identification of for example new substrates for targets, receptors for ligands, and functional materials.1-3 The concept is based on the generation of dynamic systems, in which all system components mutually undergo reversible-covalent or non-covalent interactions under thermodynamic control. The adaptive nature of these systems makes them responsive to internal or external pressures, and any changes of the important parameters in the system can rearrange the constituent compositions, leading to the amplification of optimal constituents. Among the variety of selection pressures that have been applied to dynamic systems, secondary, kinetically controlled, enzyme-catalyzed transformations have proven especially efficient in constituent selection, due to their high substrate specificities. 4-10 Lipases, which belong to the hydrolase enzyme family, were most often used in the dynamic systems owing to advantages such as showing high catalytic efficiency and good selectivities, and being environmentally friendly. to their generation and control. Yet, this represents an important development since higher order systems would lead to an increased understanding of molecular complexity in general (Fig. 1). This challenge was addressed in the present study, where new dynamic systems were generated based on two different reversible reactions operating in parallel under the same conditions, providing two types of structures for the secondary enzymatic resolution process. Several requirements need to be met by the reactions operating in such systems: (1) compatibility under the same catalytic conditions; (2) similar kinetic properties with comparable substrate distributions; and (3) no dominant side reactions taking place in the system during the time course. In the present case, the nitroaldol reaction together with hemithioacetal formation were deemed able to fulfill all prerequisites, and further evaluated in a more complex parallel resolution process. The nitroaldol reaction is one of the first C-C bond-forming reactions used for complex dynamic systems, and its reversibility has been confirmed under bas...

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confidence: 99%

Double parallel dynamic resolution through lipase-catalyzed asymmetric transformation

Zhang

Ramström

2013

Chem. Commun.

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“…This was also recently shown in a DCR study [ 4 ], where selective enzyme -mediated cyanohydrin transesterification could be used to resolve the dynamic systems and identify optimal constituents. This was also recently shown in a DCR study [ 4 ], where selective enzyme -mediated cyanohydrin transesterification could be used to resolve the dynamic systems and identify optimal constituents.…”

Section: Resolution Of Dynamic Combinatorial Cyanohydrin Libraries [ 4 ]mentioning

confidence: 57%

“…Individual Properties of Thiols(1)(2)(3)(4)(5)(6)(7)(8)(9)(10)(11)(12)(13) in Dynamic Transthiolesterification…”

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Dynamic Combinatorial Resolution

Angelin

Larsson

Vongvilai

et al. 2009

Dynamic Combinatorial Chemistry

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“…18,[21][22][23][24]27,28 It was shown that similar enantiomeric excesses (ees) could be obtained with both solvents; however, in toluene, higher conversions and reaction rates were observed. Among the enzymes tested, viz.…”

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confidence: 83%

Lipase-catalyzed asymmetric synthesis of oxathiazinanones through dynamic covalent kinetic resolution

Zhang

Ramström

2014

Org. Biomol. Chem.

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In Situ Evaluation of Lipase Performances Through Dynamic Asymmetric Cyanohydrin Resolution

Cited by 17 publications

References 56 publications

Double parallel dynamic resolution through lipase-catalyzed asymmetric transformation

Double parallel dynamic resolution through lipase-catalyzed asymmetric transformation

Dynamic Combinatorial Resolution

Lipase-catalyzed asymmetric synthesis of oxathiazinanones through dynamic covalent kinetic resolution

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