Highly efficient lipase-catalyzed asymmetric synthesis of chiral glycerol derivatives leading to practical synthesis of s-propranolol

Terao, Yoshiyasu; Murata, Masakazu; Achiwa, Kazuo; Nishio, Takeshi; Akamtsu, M.; Kamimura, Minoru

doi:10.1016/s0040-4039(00)80711-x

Cited by 96 publications

(20 citation statements)

References 13 publications

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“…In fact among all the enzymes and microorganisms studied for the stereoselective hydrolysis, RRLY-15 established its superiority with respect to high enantioselectivity and moderate rate of hydrolysis. An enzymatic resolution of 2-substituted glycerol derivatives was exploited by Achiva [37] in the synthesis of (S)-propranolol. He employed the lipase P from Pseudomonas fluorescens and examined the esterification of 2-O-benzylglycerol (14) Fig.…”

Section: B Diolsmentioning

confidence: 99%

Biocatalytic Approaches to Optically Active β-Blockers

Żelaszczyk¹,

Kieć‐Kononowicz

2007

CMC

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Beta-blockers are a very important group of drugs widely used for the treatment of cardiovascular diseases. All aryloxyaminopropanols are chiral and show different stereoselectivity in their pharmacodynamic and pharmacokinetic properties for each enantiomer. The more potent beta-adrenoceptor blocking activity is generally associated with (S)-enantiomers. Most beta-blocking agents are sold as racemates although (R)-enantiomers not only show in some cases lack of activity but might be responsible for undesirable effects. Among reports on the direct enzymatic resolution of the most representative beta-blocker propranolol, the most interesting is N-acetylation method with commercially available lipases to yield (S)-N-acetylpropranolol. Another type of the one-step (S)-isomer biocatalytic preparation from racemic mixture of propranolol is the biodegradation with the fungus. Biocatalytic methods of obtaining homochiral beta-blockers that are focused on production of versatile precursors are widely described in literature. The strategies based on the use of glycidol and derivatives as C-3 synthones have been shown to be extremely useful for the introduction of the 2-propanol chain on the aromatic system. Halohydrins are the established intermediates in the preparation of optically active beta-blockers. Its resolution by esterhydrolases has been used as a standard alternative in preparation of the homochiral propranolol. Additionally, the enzymatic resolution of the following intermediates was reported: 1-azido-3-aryloxy-2-propanols, 4-(1-aryloxy)-3-hydroxybutyric acid esters, glycerol and cyanohydrin derivatives. However, even the highly enantioselective lipase-catalyzed process can only provide 50% of the starting racemate in an optically active form. An alternative method such as a reduction of a prochiral ketone by various strains of yeast might quantitatively provide an enantiomeric product with a yield greater than 50%. The reported substrates for microbial reductions were: 1-halo-aryloxypropan-2-ones and 1-acetoxy-aryloxypropan-2-ones.

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Section: B Diolsmentioning

confidence: 99%

Biocatalytic Approaches to Optically Active β-Blockers

Żelaszczyk¹,

Kieć‐Kononowicz

2007

CMC

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“…These side effects are attributed to R-enantiomer [27]. For this reason, many authors have proposed different strategies or chemical synthesis routes to obtain (R)-and (S)-propranolol in enantiomerically pure forms [28][29][30][31]41]. However, the use of lipases has demonstrated to be a more effective strategy for obtaining pure enantiomers with higher biological activities rather than conventional chemical methods, and it has been recently established as a common strategy for the synthesis of chiral drugs [32].…”

Section: Introductionmentioning

confidence: 99%

Kinetic resolution of (R/S)-propranolol (1-isopropylamino-3-(1-naphtoxy)-2-propanolol) catalyzed by immobilized preparations of Candida antarctica lipase B (CAL-B)

et al. 2010

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“…The synthesis of the optically active glycerol part of these molecules with hydrolytic enzymes has received considerable attention in the last two years (Suemune et nl., 1986;Breitgoff, Laumen and Schneider, 1986;Kerscher and Kreiser, 1987;Terao et al, 1988). As an extension of our earlier investigation on the preparation of optically active propane-l,3-diol derivatives catalysed by porcine pancreatic lipase (PPL) (Ramos et al, 1986) we turned our attention to the preparation of the structurally similar glycerol derivatives.…”

Section: Introductionmentioning

confidence: 99%

Screening and Application of Microbial Esterases for the Enantioselective Synthesis of Chiral Glycerol Derivatives

et al. 1990

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A number of enzymes with reasonable to excellent selectivities for the conversion of prochiral 2-benzylglyceroldiacetate l c into optically active monoacetate 2c could be identified in a screening of microbial esterases and lipases. For the synthesis of the S-enantiomer of 2c by hydrolysis, two enzymes (from Aspergillus furnigatus and from Mucor juuanicus) were identified which give the product with an e.e.-value of 75%. The R-enantiomer can be obtained with a purified lipase/esterase from Pseudomonas fruorescem in 96% e.e. The optical purity of the product was determined without derivatisation by chromatography on a chiral HPLC-column.KEY WORDS Screening of microbial esterases and lipases, enzyme reaction in aqueous and organic solvent, chiral glycerol derivatives.Biocatal Biotransformation Downloaded from informahealthcare.com by University of Otago on 12/26/14For personal use only.

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Highly efficient lipase-catalyzed asymmetric synthesis of chiral glycerol derivatives leading to practical synthesis of s-propranolol

Cited by 96 publications

References 13 publications

Biocatalytic Approaches to Optically Active β-Blockers

Biocatalytic Approaches to Optically Active β-Blockers

Kinetic resolution of (R/S)-propranolol (1-isopropylamino-3-(1-naphtoxy)-2-propanolol) catalyzed by immobilized preparations of Candida antarctica lipase B (CAL-B)

Screening and Application of Microbial Esterases for the Enantioselective Synthesis of Chiral Glycerol Derivatives

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Highly efficient lipase-catalyzed asymmetric synthesis of chiral glycerol derivatives leading to practical synthesis of s-propranolol

Cited by 96 publications

References 13 publications

Biocatalytic Approaches to Optically Active &#946;-Blockers

Biocatalytic Approaches to Optically Active &#946;-Blockers

Kinetic resolution of (R/S)-propranolol (1-isopropylamino-3-(1-naphtoxy)-2-propanolol) catalyzed by immobilized preparations of Candida antarctica lipase B (CAL-B)

Screening and Application of Microbial Esterases for the Enantioselective Synthesis of Chiral Glycerol Derivatives

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Biocatalytic Approaches to Optically Active β-Blockers

Biocatalytic Approaches to Optically Active β-Blockers