Enzymes in organic synthesis. 24. Preparations of enantiomerically pure chiral lactones via stereospecific horse liver alcohol dehydrogenase catalyzed oxidations of monocyclic meso diols

Jakovac, Ignac J.; Goodbrand, H. Bruce; Lok, Kar P.; Jones, J. Bryan

doi:10.1021/ja00381a024

Cited by 199 publications

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“…Each experiment was repeated twice and the average values of the produced isomer ratios are compiled in the Table Hydrogenation of (+)-Multifidene 1 [14]. Compound (+)-1 (4.2 mg, 28.4 pmol; [a]:q8= +261") was dissolved in 0.5 ml pentane and hydrogenated as described for (+)-9b.…”

Section: { + ) -( Imentioning

confidence: 99%

Absolute Configuration of Multifidene and Viridiene, the Sperm Releasing and Attracting Pheromones of Brown Algae

Boland

Mertes

Jaenicke

et al. 1983

Helvetica Chimica Acta

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Section: { + ) -( Imentioning

confidence: 99%

Absolute Configuration of Multifidene and Viridiene, the Sperm Releasing and Attracting Pheromones of Brown Algae

Boland

Mertes

Jaenicke

et al. 1983

Helvetica Chimica Acta

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“…Stereospecific oxidations of a broad structural range of meso diols catalyzed by horse liver alcohol dehydrogenase (HLADH) represent one of the most dramatic illustrations of this approach to chiral synthon preparation (3). The complementary process of chiron production via stereospecific reductions of symmetrical diketones is of equal asymmetric synthetic interest.…”

mentioning

confidence: 99%

“…Each of the diones 1-11 possesses elements of rotational and (or) reflective symmetry, the respective symmetry elements being c2, (1,3,4), i (1, 2), uh (1,4), and a , (1,(4)(5)(6)(7)(8)(9)(10)(11). Decalins 1 , 4-10 are achiral, 2 and 11 are meso compounds, and 3 is a racemate.…”

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confidence: 99%

Enzymes in organic synthesis. 37. Preparation and characterization of potential decalindione substrates of horse liver alcohol dehydrogenase

Jones¹,

Dodds²

1987

Can. J. Chem.

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. 65, 2397 (1987).The preparations of ten decalindiones for investigation as substrates of horse liver alcohol dehydrogenase are reported The structure characterizations include clarifications of some ambiguities in the decalin literature.J. BRYAN JONES et DAVID R. DODDS. Can. J. Chem. 65, 2397Chem. 65, (1987.On a prtpark dix dtcalinediones dans le but d'examiner leur comportement comme substrats de la dkshydrogknase d'alcool provenant du foie de cheval. Les caractkrisations de leurs structures a permis de clarifier quelques ambiguitks que l'on retrouve dans la littkrature relativement aux dkcalines.[Traduit par la revue]The ability of enzymes to catalyze stereospecific transformations of symmetrical substrates into chiral synthons of value in asymmetric synthesis is now well established (2). Stereospecific oxidations of a broad structural range of meso diols catalyzed by horse liver alcohol dehydrogenase (HLADH) represent one of the most dramatic illustrations of this approach to chiral synthon preparation (3). The complementary process of chiron production via stereospecific reductions of symmetrical diketones is of equal asymmetric synthetic interest. As the first step in evaluating this aspect of HLADH stereospecificity we initiated an investigation of the enzyme's catalysis of the reductions of a series of the potential decalindione substrates 1-10 and oxidation of the meso diol 11.

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“…Unfortunately, HLADH isolated from horse liver widely applied in the 1980s for chemoselective oxidation of meso diols is no longer available [23][24][25][26]. Since commercial oxidoreductases have not indicated complete stereoselectivity, there is a need to explore microorganisms in terms of looking for a novel alcohol dehydrogenase activity [20,27].…”

Section: Introductionmentioning

confidence: 99%

Microbial Stereoselective One-Step Conversion of Diols to Chiral Lactones in Yeast Cultures

et al. 2015

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Abstract:It has been shown that whole cells of different strains of yeast catalyze stereoselective oxidation of meso diols to the corresponding chiral lactones. Among screening-scale experiments, Candida pelliculosa ZP22 was selected as the most effective biocatalyst for the oxidation of monocyclic diols 3a-b with respect to the ratio of high conversion to stereoselectivity. This strain was used in the preparative oxidation, affording enantiomerically-enriched isomers of lactones: (+)-(3aR,7aS)-cis-hexahydro-1(3H) -isobenzofuranone (2a) and (+)-(3aS,4,7,7aR)-cis-tetrahydro-1(3H)-isobenzofuranone (2b). Scaling up the culture growth, as well as biotransformation conditions has been successfully accomplished. Among more bulky substrates, bicyclic diol 3d was totally converted into enantiomerically-pure exo-bridged (+)-(3aR,4S,7R,7aS)-cis-tetrahydro-4,7-methanoisobenzofuran -1(3H)-one (2d) by Yarrovia lipolytica AR71. Microbial oxidation of diol 3f by Candida sake AM908 and Rhodotorula rubra AM4 afforded optically-pure cis-3-butylhexahydro-1(3H) -isobenzofuranone (2f), however with low conversion.

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Enzymes in organic synthesis. 24. Preparations of enantiomerically pure chiral lactones via stereospecific horse liver alcohol dehydrogenase catalyzed oxidations of monocyclic meso diols

Cited by 199 publications

References 0 publications

Absolute Configuration of Multifidene and Viridiene, the Sperm Releasing and Attracting Pheromones of Brown Algae

Absolute Configuration of Multifidene and Viridiene, the Sperm Releasing and Attracting Pheromones of Brown Algae

Enzymes in organic synthesis. 37. Preparation and characterization of potential decalindione substrates of horse liver alcohol dehydrogenase

Microbial Stereoselective One-Step Conversion of Diols to Chiral Lactones in Yeast Cultures

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