[19] Ester synthesis via acyl transfer (Transesterification)

Andersch, P.; Berger, Matthias; Hermann, Jacques; Laumen, Kurt; Lobell, Mario; Seemayer, R.; Waldinger, C.; Schneider, Manfred

doi:10.1016/s0076-6879(97)86021-1

Cited by 19 publications

(6 citation statements)

References 63 publications

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“…5, [46][47][48] In particular, this class of enzyme is able to perform enantioselective hydrolytic reactions (Table 1) and catalyzes the formation of a wide range of ester and amide bonds (Table 2) and it is in this role that they are most frequently employed. 49 A number of unusual substrates have featured recently; including resolutions of cyclophanes, 62 thioesters, 63 ferrocenes, 64 phosphonates, 65,66 helicenes, 67 and calixarenes. 68 Even lipoic acids in which the chiral centre is 5 carbon atoms from the acylated centre can be resolved.…”

Section: Acyl Transferases 21 Lipasesmentioning

confidence: 99%

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2001

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Section: Acyl Transferases 21 Lipasesmentioning

confidence: 99%

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2001

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“…Among various applications of lipases, the preparation of enantiopure drugs from their chiral intermediates using these enzymes is a subject of long‐lasting interest 12,13 . They are capable to execute stereoselective hydrolytic reactions, catalyze the production of a broad collection of amide and ester bonds, 14 and remove specific protecting groups from substrates containing multiple functionalities 15 . Versatility of lipases in organic synthesis is due to their capability to accept extensive non‐natural substrates 16,17 …”

Section: Introductionmentioning

confidence: 99%

A review on Arthrobacter sp. lipase: A versatile biocatalyst for the kinetic resolution to access enantiomerically pure/enriched compounds

et al. 2021

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Over the last few years, there has been a dramatic increase in the number of reports related to Arthrobacter sp. lipase (ABL:MTCC No. 5125) catalyzed kinetic resolution performed in biphasic media. A strain displaying esterase/lipase activity and designated as ABL was isolated, during the course of a screening program at Indian Institute of Integrative Medicine, Jammu. Considerable research has shown that reactions catalyzed by ABL are more selective than many commercial lipases. Since new applications of this lipase are emerging, there is a great need to provide all the relevant information exclusively. This review article is an attempt to cover all the relevant reports based on isolation, purification, immobilization, and application of ABL in the biopharmaceutical sector.

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“…Moreover, the presence of biocatalysts can promote reactions that introduce a chiral center in the molecule with high chemoselectivity, regioselectivity, and enantioselectivity at mild reaction conditions . Numerous organic reactions have reported the use of biocatalytic protocols, such as hydrolytic reactions of esters and amides, transesterification reactions, oligosaccharide syntheses, acylation of chlorohydrins, nitrile biodegradations, Baeyer‐Villiger oxidations, aldol condensations, polymerizations, industrial applications, and Knoevenagel condensations …”

Section: Introductionmentioning

confidence: 99%

Enantioselective ene‐reduction of E‐2‐cyano‐3‐(furan‐2‐yl) acrylamide by marine and terrestrial fungi and absolute configuration of (R)‐2‐cyano‐3‐(furan‐2‐yl) propanamide determined by calculations of electronic circular dichroism (ECD) spectra

et al. 2019

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This work reports the green organic chemistry synthesis of E‐2‐cyano‐3(furan‐2‐yl) acrylamide under microwave radiation (55 W), as well as the use of filamentous marine and terrestrial‐derived fungi, in the first ene‐reduction of 2‐cyano‐3‐(furan‐2‐yl) acrylamide to (R)‐2‐cyano‐3‐(furan‐2‐yl)propanamide. The fungal strains screened included Penicillium citrinum CBMAI 1186, Trichoderma sp. CBMAI 932 and Aspergillus sydowii CBMAI 935, and the filamentous terrestrial fungi Aspergillus sp. FPZSP 146 and Aspergillus sp. FPZSP 152. A compound with an uncommon CN‐bearing stereogenic center at the α‐C position was obtained by enantioselective reactions mediated in the presence of the microorganisms yielding the (R)‐2‐cyano‐3‐(furan‐2‐yl) propanamide 3a. Its isolated yield and e.e. ranged from 86% to 98% and 39% to 99%, respectively. The absolute configuration of the biotransformation products was determined by time‐dependent density functional theory (TD‐DFT) calculations of electronic circular dichroism (ECD) spectra. Finally, the tautomerization of 2‐cyano‐3‐(furan‐2‐yl) propanamide 3a to form an achiral ketenimine was observed and investigated in presence of protic solvents.

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[19] Ester synthesis via acyl transfer (Transesterification)

Cited by 19 publications

References 63 publications

Untitled

Untitled

A review on Arthrobacter sp. lipase: A versatile biocatalyst for the kinetic resolution to access enantiomerically pure/enriched compounds

Enantioselective ene‐reduction of E‐2‐cyano‐3‐(furan‐2‐yl) acrylamide by marine and terrestrial fungi and absolute configuration of (R)‐2‐cyano‐3‐(furan‐2‐yl) propanamide determined by calculations of electronic circular dichroism (ECD) spectra

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