Preparation of the Monoacylates of 2-Substituted (<i>Z</i>)-But-2-ene-1,4-diols Using Porcine Pancreas Lipase

Kawashima, Yuya; Ezawa, Tetsuya; Harada, T.; Noguchi, Takuya; Kawasaki, Masashi; Kirihara, Masayuki; Imai, Nobuyuki

doi:10.1246/bcsj.20150303

Cited by 5 publications

(3 citation statements)

References 18 publications

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“…Lipases derived from the porcine pancreas play a significant role in preparing Monoacylates of 2-Substituted (Z)-But-2-ene-1,4-diols (Kawashima et al, 2016), asymmetric aldol reactions (J. , and the synthesis of bis (indolyl) alkanes (Xiang et al, 2013). Furthermore, starfish lipases are a viable substitute for porcine pancreatic lipases and have significant uses in the food processing sector, as shown in Table 3.…”

Section: Animal and Insect Sourcesmentioning

confidence: 99%

Lipases: Sources, immobilization techniques, and applications

Hussain,

Khan,

Jiang

et al. 2023

IJEAB

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Enzymes serve as natural catalysts that exhibit high specificity to their respective substrates and function effectively under mild temperature, pressure, and pH conditions, resulting in superior conversion rates compared to traditional chemical catalysts. These catalysts, sourced from animals, plants, and microorganisms, offer versatility, with lipases standing out for their broad applicability, capturing the interest of various industries. However, the widespread adoption of soluble lipases is hindered by challenges such as high acquisition costs, limited operational stability, and difficulties in recovery and reuse. To address these limitations, enzymatic immobilization has emerged as a viable alternative, aiming to enhance the stability of soluble enzymes while simplifying their recovery and reuse processes. This approach significantly mitigates the overall cost associated with enzyme-dependent processes. This review examines the diverse sources of enzymes, explores various immobilization methods for lipases, and discusses their wide-ranging applications.

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Section: Animal and Insect Sourcesmentioning

confidence: 99%

Lipases: Sources, immobilization techniques, and applications

Hussain,

Khan,

Jiang

et al. 2023

IJEAB

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“…Amongst the various animal lipases, pancreatic lipase has been extensively used as a research tool in the fields of lipid chemistry as well as biochemistry as it effectively catalyze the hydrolysis of primary alcohol esters . Lipases derived from porcine pancreas are used in the preparation of the Monoacylates of 2‐Substituted (Z)‐But‐2‐ene‐1,4‐diols, asymmetric aldol reactions , synthesis of bis (indolyl) alkanes . Further, Lipases derived from star fish are found to be an alternative to porcine pancreas lipases, which find their major application in food processing industries as mentioned in Table .…”

Section: Sources Of Lipasesmentioning

confidence: 99%

Recent advances on sources and industrial applications of lipases

Sarmah

Revathi

Sheelu

et al. 2017

Biotechnology Progress

273

148

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Lipases are the industrially important biocatalysts, which are envisioned to have tremendous applications in the manufacture of a wide range of products. Their unique properties such as better stability, selectivity and substrate specificity position them as the most expansively used industrial enzymes. The research on production and applications of lipases is ever growing and there exists a need to have a latest review on the research findings of lipases. The present review aims at giving the latest and broadest overall picture of research and development on lipases by including the current studies and progressions not only in the diverse industrial application fields of lipases, but also with regard to its structure, classification and sources. Also, a special emphasis has been made on the aspects such as process optimization, modeling, and design that are very critical for further scale-up and industrial implementation. The detailed tabulations provided in each section, which are prepared by the exhaustive review of current literature covering the various aspects of lipase including its production and applications along with example case studies, will serve as the comprehensive source of current advancements in lipase research. This review will be very useful for the researchers from both industry as well as academia in promoting lipolysis as the most promising approaches to intensified, greener and sustainable processes. © 2017 American Institute of Chemical Engineers Biotechnol. Prog., 34:5-28, 2018.

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“…( Z )‐2‐Butene‐1,4‐diol monoesters are key intermediates in organic synthesis, though surprisingly, apart from rare synthetic methods relying on enzymatic deacylation of ( Z )‐2‐butene‐1,4‐diol diesters using porcine pancreas lipase (PPL) (Scheme 2, path a) [16] lipase PS‐D (Pseudomonas cepacian, Amano) (path b) [17] or the enzymatic acylation of ( Z )‐2‐butene‐1,4‐diols with different vinyl acylates using PPL (path c), [16,17b] currently there is no other general methodology available that provides simple access to a wide range of ( Z )‐2‐butene‐1,4‐diol monoesters.…”

Section: Introductionmentioning

confidence: 99%

Chemo‐, Regio‐ and Stereoselective Preparation of (Z)‐2‐Butene‐1,4‐Diol Monoesters via Pd‐Catalyzed Decarboxylative Acyloxylation

Cheng,

Zhao,

Zhang

et al. 2024

Chemistry A European J

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(Z)‐alkenes are useful synthons but thermodynamically less stable than their (E)‐isomers and typically more difficult to prepare. The synthesis of 1,4‐hetero‐bifunctionalized (Z)‐alkenes is particularly challenging due to the inherent regio‐ and stereoselectivity issues. Herein we demonstrate a general, chemoselective and direct synthesis of (Z)‐2‐butene‐1,4‐diol monoesters. The protocol operates within a Pd‐catalyzed decarboxylative acyloxylation regime involving vinyl ethylene carbonates (VECs) and various carboxylic acids as the reaction partners under mild and operationally attractive conditions. The newly developed process allows access to a structurally diverse pool of (Z)‐2‐butene‐1,4‐diol monoesters in good yields and with excellent regio‐ and stereoselectivity. Various synthetic transformations of the obtained (Z)‐2‐butene‐1,4‐diol monoesters demonstrate how these synthons are of great use to rapidly diversify the portfolio of these formal desymmetrized (Z)‐alkenes.

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Preparation of the Monoacylates of 2-Substituted (Z)-But-2-ene-1,4-diols Using Porcine Pancreas Lipase

Cited by 5 publications

References 18 publications

Lipases: Sources, immobilization techniques, and applications

Lipases: Sources, immobilization techniques, and applications

Recent advances on sources and industrial applications of lipases

Chemo‐, Regio‐ and Stereoselective Preparation of (Z)‐2‐Butene‐1,4‐Diol Monoesters via Pd‐Catalyzed Decarboxylative Acyloxylation

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