Identification and Optimisation of Lipase-Catalysed Synthesis of Betulinic Acid Amide in a Solvent System

Yusof, Nurul Atikah Binti Amin; Hadzir, Nursyamsyila Mat; Ashari, Siti Efliza

doi:10.1155/2016/5149326

Cited by 2 publications

(2 citation statements)

References 12 publications

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“…Novoenzym 435 from Candida antartica was used as a catalyst for enzymatic amidation, and butylamine was used as an amine reagent that was coupled with betulinic acid ( 5 ). Using the optimal conditions gave the product in 64.6% yield ( Scheme 11 ) [ 128 ].…”

Section: Enzymatic Modification Of Betulinic Acid (5) and Betulin (8)mentioning

confidence: 99%

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Biocatalysis in the Chemistry of Lupane Triterpenoids

Bachořík

Urban

2021

Molecules

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Pentacyclic triterpenes are important representatives of natural products that exhibit a wide variety of biological activities. These activities suggest that these compounds may represent potential medicines for the treatment of cancer and viral, bacterial, or protozoal infections. Naturally occurring triterpenes usually have several drawbacks, such as limited activity and insufficient solubility and bioavailability; therefore, they need to be modified to obtain compounds suitable for drug development. Modifications can be achieved either by methods of standard organic synthesis or with the use of biocatalysts, such as enzymes or enzyme systems within living organisms. In most cases, these modifications result in the preparation of esters, amides, saponins, or sugar conjugates. Notably, while standard organic synthesis has been heavily used and developed, the use of the latter methodology has been rather limited, but it appears that biocatalysis has recently sparked considerably wider interest within the scientific community. Among triterpenes, derivatives of lupane play important roles. This review therefore summarizes the natural occurrence and sources of lupane triterpenoids, their biosynthesis, and semisynthetic methods that may be used for the production of betulinic acid from abundant and inexpensive betulin. Most importantly, this article compares chemical transformations of lupane triterpenoids with analogous reactions performed by biocatalysts and highlights a large space for the future development of biocatalysis in this field. The results of this study may serve as a summary of the current state of research and demonstrate the potential of the method in future applications.

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Section: Enzymatic Modification Of Betulinic Acid (5) and Betulin (8)mentioning

confidence: 99%

“… Optimal conditions for enzymatic amidation of betulinic acid [ 128 ]. Reagents and conditions: (i) butyl amine (1 eq.…”

Section: Figures Schemes and Tablesmentioning

confidence: 99%

Biocatalysis in the Chemistry of Lupane Triterpenoids

Bachořík

Urban

2021

Molecules

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Effect of Reaction Parameters on the Lipase-Catalyzed Kinetic Resolution of (RS )-Metoprolol

Rajin

Zulkifli

Abang

et al. 2020

AJChE

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Racemic metoprolol is a selective ß1-blocker, which is used in cardiovascular disease treatment. It has been found that (S)-metoprolol has a higher affinity to bind the ß-adrenergic receptor compared to (R)-metoprolol. Moreover, the regulatory authorities’ high market demand and guidelines have increased the preference for single enantiomer drugs. In this work, the lipase-catalyzed kinetic resolution of racemic metoprolol was performed to obtain the desired enantiomer. The type of lipase, acyl donor, and solvent were screened out. This was achieved by Candida antarctica B lipase-catalyzed transesterification of racemic metoprolol in hexane and vinyl acetate as the solvent and an acyl donor, which gave maximum conversion of (S)-metoprolol (XS) of 52%, enantiomeric excess of substrate, (ees) of 92% and product (eeP) of 90% with enantiomeric ratio (E) of 62. This method can be considered as green chemistry, which can be applied to produce other enantiopure beta-blockers.

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Identification and Optimisation of Lipase-Catalysed Synthesis of Betulinic Acid Amide in a Solvent System

Cited by 2 publications

References 12 publications

Biocatalysis in the Chemistry of Lupane Triterpenoids

Biocatalysis in the Chemistry of Lupane Triterpenoids

Effect of Reaction Parameters on the Lipase-Catalyzed Kinetic Resolution of (RS )-Metoprolol

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