Efficient regioselective synthesis of 3′‐<i>O</i>‐crotonylfloxuridine catalysed by <i>Pseudomonas cepacia</i> lipase

Zhao, Zhilei; Zong, Min‐Hua; Li, Ning

doi:10.1042/ba20080018

Cited by 7 publications

(3 citation statements)

References 34 publications

(33 reference statements)

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“…The authors evaluated the lipase selectivity toward various acyl donors, and they verified an increase in 3‐regioselectivity with increased acyl chain length. Zhao, Zong, and Li () also studied the regioselective acylation of FUdR with vinyl crotonate as the acyl donor and catalyzed by Lipase PS‐C. A simple and environmentally friendly process allowed to obtain 3′‐O‐crotonylfloxuridine with a high yield under mild reaction conditions.…”

Section: Synthesis Of Drugsmentioning

confidence: 99%

Burkholderia cepacia lipase: A versatile catalyst in synthesis reactions

Sánchez

Tonetto

Ferreira

2017

Biotech & Bioengineering

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The lipase from Burkholderia cepacia, formerly known as Pseudomonas cepacia lipase, is a commercial enzyme in both soluble and immobilized forms widely recognized for its thermal resistance and tolerance to a large number of solvents and short-chain alcohols. The main applications of this lipase are in transesterification reactions and in the synthesis of drugs (because of the properties mentioned above). This review intends to show the features of this enzyme and some of the most relevant aspects of its use in different synthesis reactions. Also, different immobilization techniques together with the effect of various compounds on lipase activity are presented. This lipase shows important advantages over other lipases, especially in reaction media including solvents or reactions involving short-chain alcohols.

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Section: Synthesis Of Drugsmentioning

confidence: 99%

Burkholderia cepacia lipase: A versatile catalyst in synthesis reactions

Sánchez

Tonetto

Ferreira

2017

Biotech & Bioengineering

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“…However, few reports on the enzymatic synthesis of undecylenic acid esters of polyhydroxylated compounds have appeared (Tokiwa et al 2007a, b;Raku et al 2003). More importantly, mild enzymatic acylation would effectively avoid the isomerization of the double bond (Diaz-Rodriguez et al 2005;Zhao et al 2009), which is crucial to the biological activities of the unsaturated fatty acid. Herein, we reported the first enzymatic synthesis of undecylenic acid esters of purine nucleosides, potential dual prodrugs.…”

Section: Introductionmentioning

confidence: 99%

Highly regioselective synthesis of undecylenic acid esters of purine nucleosides catalyzed by Candida antarctica lipase B

Gao

Zong

2011

Biotechnol Lett

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Regioselective undecylenoylation of purine nucleosides as potential dual prodrugs was achieved by Candida antarctica lipase B using adenosine as a model reactant. The optimum organic solvent, molar ratio of vinyl ester to nucleoside, enzyme dosage, reaction temperature and molecular sieve amount were anhydrous THF, 5:1, 20 U/ml, 45°C and 75 mg/ml, respectively. Under the optimum conditions, the initial reaction rate, yield and 5'-regioselectivity were 1.1 mM/h, 90% and >99%, respectively. The enzymatic acylation of various nucleosides furnished the desired 5'-ester derivatives with the yields of 60-95% and 5'-regioselectivities of >99%. In addition, the lipase displayed excellent operational stability in THF, and retained 96% of its initial activity after reused for five batches.

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“…To date, enzymatic acylation of nucleosides in organic media has emerged as a promising procedure, owing to its advantageous properties, including high regioselectivity, mild reaction conditions and environmental friendliness [9–11]. Ferrero and Gotor [12,13] have reviewed the use of biocatalysts for the modification of nucleosides.…”

Section: Introductionmentioning

confidence: 99%

Efficiently enhancing regioselective acylation of 5‐azacytidine catalysed by Candida antarctica lipase B with co‐solvent mixtures as the reaction media

Zong

Chen

2009

Biotech and App Biochem

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A comparative study of regioselective acylation of 5-azacytidine catalysed by CAL-B (Candida antarctica lipase B) in co-solvent mixtures and in pure organic solvents was performed, to our knowledge for the first time, and it was shown that a remarkable enhancement in the initial rate and substrate conversion in the reaction could be achieved with co-solvents as the reaction medium instead of pure organic solvents. For the CAL-B-catalysed regioselective synthesis of 5'-O-butyryl-5-azacytidine in co-solvent mixtures, the optimal conditions were as follows: optimal co-solvent mixture, hexane/pyridine (40/60, v/v); initial aw (water activity), 0.07; enzyme dosage, 50 units/ml; vinyl butyrate/5-azacytidine molar ratio, 15:1; temperature, 60 °C. Under the optimal conditions, v0 (the initial reaction rate), C (the substrate conversion) and the regioselectivity of the reaction were 0.75 mM/min, 99.0% and above 99% respectively. Similar phenomena were observed in the CAL-B-catalysed regioselective acylation of 5-azacytidine with an extensive range of fatty acid vinyl esters (from C2 to C18). Compared with pure pyridine, the reactions were greatly accelerated in a hexane/pyridine (40/60, v/v) co-solvent mixture and 5-azacytidine could be biotransformed into its derivative 5'-O-acyl-5-azacytidine at a much higher conversion rate (91.4-99.0% as against 40.2-43.5%). Meanwhile, adoption of a co-solvent mixture as the reaction medium could also greatly lower the enzyme dosage and the molar ratio of acyl donor to 5-azacytidine.

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Efficient regioselective synthesis of 3′‐O‐crotonylfloxuridine catalysed by Pseudomonas cepacia lipase

Cited by 7 publications

References 34 publications

Burkholderia cepacia lipase: A versatile catalyst in synthesis reactions

Burkholderia cepacia lipase: A versatile catalyst in synthesis reactions

Highly regioselective synthesis of undecylenic acid esters of purine nucleosides catalyzed by Candida antarctica lipase B

Efficiently enhancing regioselective acylation of 5‐azacytidine catalysed by Candida antarctica lipase B with co‐solvent mixtures as the reaction media

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