Biocatalytic resolution of a tertiary quinuclidinol ester using Pig liver esterase

Coope, John F.; Main, Brian G.

doi:10.1016/0957-4166(95)00172-l

Cited by 13 publications

(4 citation statements)

References 16 publications

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“…A third structure that describes the adsorption of acetylene in a porous cucurbituril (KOBNIZ; Lim et al, 2008) that features an sp-C-HÁ Á ÁO carbonyl interaction is best described as an inclusion complex since the acetylene enters accessible void space in the porous cucurbitril structure. Four of the other structures are salts in which the sp-C-HÁ Á ÁO interaction is secondary [refcodes COBKUZ (Steiner et al, 1999), PEBPER (Wheeler & Foxman, 1992), SAXGUV (Laus et al, 2012), and ZEWXII (Coope & Main, 1995)], while one structure includes conventional (O-HÁ Á ÁO) hydrogen bonding as the major intermolecular force in the cocrystal (AJAGEX; Luo & Palmore, 2002). One structure is a methanol solvate of a complex tetracyclic molecule containing a terminal alkyne and an ester group that have an sp-C-HÁ Á ÁO(carbonyl) interaction between like molecules (VOLKIS; Duax et al, 2014).…”

Section: Research Papersmentioning

confidence: 99%

Cocrystals of 1,4-diethynylbenzene with 1,3-diacetylbenzene and benzene-1,4-dicarbaldehyde exhibiting strong nonconventional alkyne–carbonyl C—H...O hydrogen bonds between the components

Bosch

2016

Acta Crystallogr C

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Weak interactions between organic molecules are important in solid-state structures where the sum of the weaker interactions support the overall three-dimensional crystal structure. The sp-C-H...N hydrogen-bonding interaction is strong enough to promote the deliberate cocrystallization of a series of diynes with a series of dipyridines. It is also possible that a similar series of cocrystals could be formed between molecules containing a terminal alkyne and molecules which contain carbonyl O atoms as the potential hydrogen-bond acceptor. I now report the crystal structure of two cocrystals that support this hypothesis. The 1:1 cocrystal of 1,4-diethynylbenzene with 1,3-diacetylbenzene, CH·CHO, (1), and the 1:1 cocrystal of 1,4-diethynylbenzene with benzene-1,4-dicarbaldehyde, CH·CHO, (2), are presented. In both cocrystals, a strong nonconventional ethynyl-carbonyl sp-C-H...O hydrogen bond is observed between the components. In cocrystal (1), the C-H...O hydrogen-bond angle is 171.8 (16)° and the H...O and C...O hydrogen-bond distances are 2.200 (19) and 3.139 (2) Å, respectively. In cocrystal (2), the C-H...O hydrogen-bond angle is 172.5 (16)° and the H...O and C...O hydrogen-bond distances are 2.25 (2) and 3.203 (2) Å, respectively.

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Section: Research Papersmentioning

confidence: 99%

Cocrystals of 1,4-diethynylbenzene with 1,3-diacetylbenzene and benzene-1,4-dicarbaldehyde exhibiting strong nonconventional alkyne–carbonyl C—H...O hydrogen bonds between the components

Bosch

2016

Acta Crystallogr C

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“…(4A)). Several routes have been reported for the chemical and biocatalytic production of 14 [68][69][70][71]. Among these methods, kinetic resolution of a racemic mixture of n-butyl-3-quinuclidinol through enantioselective hydrolysis with Aspergillus melleus protease has been used for industrial production with an overall yield of 42% and an optical purity of 96% e.e.…”

Section: Talsaclidine and Revatropatementioning

confidence: 99%

Dehydrogenases/Reductases for the Synthesis of Chiral Pharmaceutical Intermediates

Huang¹,

Liu²,

Wu³

et al. 2010

COC

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The increasing trend of chiral drugs in the pharmaceutical industry has promoted greatly on the development of numerous biocatalytic routes in combination with chemical methods. Because the resulting chiral alcohols are particularly valuable intermediates and precursors for the synthesis of chiral drugs, dehydrogenases and reductases have been extensively used in the synthesis of chiral compounds from ketone substrates with high regio-and stereo-selectivities. In this review, biocatalytic processes carried out by dehydrogenases and reductases are described for the synthesis of chiral intermediates for a wide variety of pharmaceuticals, including antidepressants, anti-anxieties, anti-asthmatics, anti-hypertensives, cholesterol-lowering agents, NK1 antagonists, ACE inhibitors andLactamase inhibitors.

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“…27 The well known pig liver esterase (PLE) can also be used to resolve tertiary alcohols. Coope and Main reported PLE‐catalysed enantioselective kinetic resolutions of quinuclidine esters to produce chiral tertiary esters in acceptable yields (for a kinetic resolution) and enantioselectivities (Scheme ) 28…”

Section: Lipases and Esterasesmentioning

confidence: 99%

Enzymatic Synthesis of Optically Active Tertiary Alcohols: Expanding the Biocatalysis Toolbox

Kourist¹,

Marı́a²,

Bornscheuer³

2008

ChemBioChem

114

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Enantiopure tertiary alcohols are very valuable building blocks for the synthesis of many different natural products and pharmaceuticals. As a consequence, several chemical and enzymatic strategies to afford such chiral structures have been described. Promising enzymatic approaches with agents such as epoxide hydrolases, dehalogenases and hydroxynitrile lyases have been reported, as well as dihydroxylation by microorganisms. Apart from those valuable options, the hydrolase-based kinetic resolution of tertiary alcohols has been known for the last three decades, as several wild-type enzymes have been reported to be able to accept these sterically hindered molecules. More recently, the existence of an amino acid motif within an enzyme's active site has been identified as highly relevant for the acceptance of such bulky structures. This discovery clearly facilitates the identification of novel biocatalysts for this application. Although several tertiary alcohols have been successfully resolved with wild-type biocatalysts, enantioselectivities have often been too low for synthetic purposes. These limitations have recently been overcome by accessing enzymes from the metagenome through directed evolution or by rational protein design. This minireview describes the state of the art in this area, highlighting aspects of basic academic research into the practical application of biocatalysts for the synthesis of optically active tertiary alcohols.

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Biocatalytic resolution of a tertiary quinuclidinol ester using Pig liver esterase

Cited by 13 publications

References 16 publications

Cocrystals of 1,4-diethynylbenzene with 1,3-diacetylbenzene and benzene-1,4-dicarbaldehyde exhibiting strong nonconventional alkyne–carbonyl C—H...O hydrogen bonds between the components

Cocrystals of 1,4-diethynylbenzene with 1,3-diacetylbenzene and benzene-1,4-dicarbaldehyde exhibiting strong nonconventional alkyne–carbonyl C—H...O hydrogen bonds between the components

Dehydrogenases/Reductases for the Synthesis of Chiral Pharmaceutical Intermediates

Enzymatic Synthesis of Optically Active Tertiary Alcohols: Expanding the Biocatalysis Toolbox

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