Synthesis of Chirally Pure Enantiomers by Lipase

Bhardwaj, Kamal Kumar; Gupta, Reena

doi:10.5650/jos.ess17114

Cited by 25 publications

(13 citation statements)

References 92 publications

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“…In another patent from Wuxi Fortune Pharmaceutical Co., Ltd., granted in 2018 [114], the gram-scale kinetic resolution (Scheme 11) of racemic hidroxynitrile (R,S)-24, obtained from racemic epyclorhydrine (R,S)-23, was reported using an enzymatic transesterification with perchlorophenyl acetate and lipase B from C. antarctica, supported on an acid resin (Novozym 435? ), to obtain acetate (R)-25, which hydrolysis leads to L-carnitine, an essential co-factor in the metabolism of lipids involved in the generation of cellular energy [115,116] The resolution of chiral amines is a very attractive research area, because of the plethora of applications described for such enantiopure compounds [117,118], which can be obtained by using oxidoreductases [119] (see Section 3.2), transaminases [120] (Section 4), and lipases [121,122], as we will comment here. In fact, different companies have been actively working in this area during the last years.…”

Section: Stereoselective Acyl-transfer Catalyzed By Lipasesmentioning

confidence: 99%

Biocatalysis as Useful Tool in Asymmetric Synthesis: An Assessment of Recently Granted Patents (2014–2019)

Marı́a¹,

Gonzalo

Alcántara

2019

Catalysts

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The broad interdisciplinary nature of biocatalysis fosters innovation, as different technical fields are interconnected and synergized. A way to depict that innovation is by conducting a survey on patent activities. This paper analyses the intellectual property activities of the last five years (2014–2019) with a specific focus on biocatalysis applied to asymmetric synthesis. Furthermore, to reflect the inventive and innovative steps, only patents that were granted during that period are considered. Patent searches using several keywords (e.g., enzyme names) have been conducted by using several patent engine servers (e.g., Espacenet, SciFinder, Google Patents), with focus on granted patents during the period 2014–2019. Around 200 granted patents have been identified, covering all enzyme types. The inventive pattern focuses on the protection of novel protein sequences, as well as on new substrates. In some other cases, combined processes, multi-step enzymatic reactions, as well as process conditions are the innovative basis. Both industries and academic groups are active in patenting. As a conclusion of this survey, we can assert that biocatalysis is increasingly recognized as a useful tool for asymmetric synthesis and being considered as an innovative option to build IP and protect synthetic routes.

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Section: Stereoselective Acyl-transfer Catalyzed By Lipasesmentioning

confidence: 99%

Biocatalysis as Useful Tool in Asymmetric Synthesis: An Assessment of Recently Granted Patents (2014–2019)

Marı́a¹,

Gonzalo

Alcántara

2019

Catalysts

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“…They are used for protection of functional groups, for separation of racemic mixtures in the production of enantioisomers, for transesterification in the field of fine organic synthesis, and are hence useful for the pharmaceutical, cosmetic, and chemical industries [38]. These enzymes are characterized by selectivity to the type and position of the fatty acids in the esters, enantiospecificity (specificity in stereoisomer synthesis), and ability to catalyze heterogeneous reactions between two phases -water-soluble and water-insoluble.…”

Section: Lipase Produced By G Stearothermophilus Mc7mentioning

confidence: 99%

“…These enzymes are characterized by selectivity to the type and position of the fatty acids in the esters, enantiospecificity (specificity in stereoisomer synthesis), and ability to catalyze heterogeneous reactions between two phases -water-soluble and water-insoluble. They are used for protection of functional groups, for separation of racemic mixtures in the production of enantioisomers, for transesterification in the field of fine organic synthesis, and are hence useful for the pharmaceutical, cosmetic, and chemical industries [38]. Methyl and ethyl esters with long chain fatty acids are valuable for the production of fuel, detergents, and lubricants.…”

Section: Lipase Produced By G Stearothermophilus Mc7mentioning

confidence: 99%

Thermostable enzymes and polysaccharides produced by thermophilic bacteria isolated from Bulgarian hot springs

Kambourova

2018

Engineering in Life Sciences

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Thermostable enzymes (thermozymes) have been recognized as extremophilic compounds with a greatest biotechnological importance in different industrial areas. Quite recently exopolysaccharides (EPSs) synthesized by thermophiles became an object of increased research interest due to their unique properties appropriate for some specific industrial needs. Thermophilic producers of biotechnologically valuable enzymes and novel EPS were isolated by our group from Bulgarian thermal springs with a diverse geotectonic origin and different water properties. Laboratory reactor processes for their production were developed in batch and continuous cultures. Some of the synthesized thermostable enzymes were among the first described in their groups, for example, the single known thermostable gellan lyase that demonstrated specific activity higher than that of the mesophilic enzymes. Isolated by us thermostable xylanase was able to degrade more than 60% of beechwood xylan in a coprocess with an archaeal β‐xylosidase. Lipase purified by us was active between 55 and 90°C with an optimum at 75–80°C in a large pH range. It was able to degrade a broad range of substrates. Isolates from Bulgarian hot springs synthesized EPS with novel composition and high thermostability. Thus, Bulgarian hot springs harbor a wide set of thermophilic producers of novel enzymes and EPS with potential for a large number of biotechnological applications.

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“…1,2 Enzymatic kinetic resolution is one of the most potent and important method to access enantiopure compounds 3,4 and is widely used for the synthesis of chiral intermediates for pharmaceutical chemistry 5,6 where approximately 80% of the drugs currently under development are chiral. 7,8 Lipases (EC 3.1.1.3) are the most widely employed biocatalysts and have high industrial potential for the synthesis of enantiomerically pure compounds especially by transesterification in organic solvents or by hydrolysis in aqueous or biphasic media. 9,10 Enantiopure (hydroxyalkyl)phenols and their derivatives are important synthetic intermediates to develop drugs, 11,12 thus highlighting the industrial interest.…”

Section: Introductionmentioning

confidence: 99%

“…The use of lipases in organic synthesis makes it possible to obtain enantiopure building blocks under mild, ecological, and environmentally friendly conditions . Enzymatic kinetic resolution is one of the most potent and important method to access enantiopure compounds and is widely used for the synthesis of chiral intermediates for pharmaceutical chemistry where approximately 80% of the drugs currently under development are chiral . Lipases (EC 3.1.1.3) are the most widely employed biocatalysts and have high industrial potential for the synthesis of enantiomerically pure compounds especially by transesterification in organic solvents or by hydrolysis in aqueous or biphasic media .…”

Section: Introductionmentioning

confidence: 99%

Efficient access to both enantiomers of 3‐(1‐hydroxyethyl)phenol by regioselective and enantioselective CAL‐B–catalyzed hydrolysis of diacetate in organic media by sodium carbonate

2018

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In the present paper, we describe several pathways employing immobilized lipase from Candida antarctica B (CAL‐B) as biocatalyst to prepare easily both enantiomers of 3‐(1‐hydroxyethyl)phenol. We have applied hydrolysis with Na2CO3 in organic media under mild conditions. The reaction parameters solvent effect, amount of lipase, and Na2CO3 were examined with 3‐(1‐acetoxyethyl)phenyl acetate as substrate. In alkaline hydrolysis, (R)‐3‐(1‐hydroxyethyl)phenol was obtained with ee = 99% and (S)‐(−)‐3‐(1‐acetoxyethyl)phenol with ee = 98% at optimal conversion (c = 50%) and high selectivity (E > 200). Two other deacylation reactions were compared: alcoholysis with MeOH and with NEt3. The acylation of 3‐(1‐hydroxyethyl)phenol with vinyl acetate was also examined. Alkaline hydrolysis gave the best results, while good regioselectivity and enantioselectivity were observed in alcoholysis and acylation reactions. Finally, (S)‐ and (R)‐3‐(1‐hydroxyethyl)phenol (ee > 98%), key intermediates for the synthesis of important drugs, were prepared from the corresponding racemic diacetate through alkaline hydrolysis.

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Synthesis of Chirally Pure Enantiomers by Lipase

Cited by 25 publications

References 92 publications

Biocatalysis as Useful Tool in Asymmetric Synthesis: An Assessment of Recently Granted Patents (2014–2019)

Biocatalysis as Useful Tool in Asymmetric Synthesis: An Assessment of Recently Granted Patents (2014–2019)

Thermostable enzymes and polysaccharides produced by thermophilic bacteria isolated from Bulgarian hot springs

Efficient access to both enantiomers of 3‐(1‐hydroxyethyl)phenol by regioselective and enantioselective CAL‐B–catalyzed hydrolysis of diacetate in organic media by sodium carbonate

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