TITLE

Regioselective enzymatic acylation of ribavirin to give potential multifunctional derivatives

AUTHOR(S)
Bo-Kai Liu; Na Wang; Qi Wu; Chuan-Ying Xie; Xian-Fu Lin
PUB. DATE
May 2005
SOURCE
Biotechnology Letters;May2005, Vol. 27 Issue 10, p717
SOURCE TYPE
Academic Journal
DOC. TYPE
Article
ABSTRACT
Lipase-catalyzed synthesis of potential multifunctional ribavirin derivatives was performed in acetone. Divinyl dicarboxylates with different chain lengths (C4, C6, C9, C10) were used as acyl donors and the reactions were catalyzed by lipase immobilized on acrylic resin from Candida antarctica (CAL-B). Ribavirin was regioselectivly acylated at the primary hydroxyl groups and the corresponding vinyl esters (C4, C6, C9, C10) were prepared in respective yields of 48%, 65%, 54%, 55%.
ACCESSION #
17744526

 

Related Articles

  • Supercritical CO2 as a reaction medium for synthesis of capsaicin analogues by lipase-catalyzed transacylation of capsaicin. Kobata, Kenji; Kobayashi, Mamiko; Kinpara, Sachiyo; Watanabe, Tatsuo // Biotechnology Letters;Sep2003, Vol. 25 Issue 18, p1575 

    Capsaicin analogues having different acyl moiety were synthesized by lipase-catalyzed transacylation of capsaicin with a corresponding acyl donor in supercritical CO2 as a reaction medium. Transacylation with methyl tetradecanoate using Novozym 435 as a catalyst gave vanillyl tetradecanamide in...

  • Synthesis of Isopropyl Ferulate Using Silica-Immobilized Lipase in an Organic Medium. Kumar, Ashok; Kanwar, Shamsher Singh // Enzyme Research;2011, p1 

    Immobilization of lipases has proved to be a useful technique for improving an enzyme's activity in organic solvents. In the present study, the performance of a silica-immobilized lipase was evaluated for the synthesis of isopropyl ferulate in DMSO. The biocatalyst was cross-linked onto the...

  • Lipase-catalyzed simultaneous biosynthesis of biodiesel and glycerol carbonate from corn oil in dimethyl carbonate. Ji Young Min; Eun Yeol Lee // Biotechnology Letters;Sep2011, Vol. 33 Issue 9, p1789 

    Biodiesel [fatty acid methyl esters (FAMEs)] and glycerol carbonate were synthesized from corn oil and dimethyl carbonate (DMC) via transesterification using lipase (Novozyme 435) in solvent-free reaction in which excess DMC was used as the substrate and reaction medium. Glycerol carbonate was...

  • Lipase-catalyzed regioselective synthesis of steryl (6′- O-acyl)glucosides. Paczkowski, Cezary; Musial, Arkadiusz; Wlodkowski, Leszek; Kalinowska, Malgorzata; Wojciechowski, Zdzislaw // Biotechnology Letters;Sep2007, Vol. 29 Issue 9, p1403 

    The regioselective acylation of cholesteryl β- d-glucoside, at the C-6 of the glucose moiety, was achieved using microbial lipases in organic solvents. With palmitic acid as an acyl donor 81 or 63% conversions of cholesteryl glucoside to its 6′- O-palmitoyl derivative were obtained...

  • Regio- and stereo-selectively kinetic resolution of four stereoisomers of 1-phenylbutan-1,3-diol by Candida rugosa lipase. Yi-Hui Chen; Joly, S.; Pin-Mei Huang; Kuangsen Sung // Canadian Journal of Chemistry;Aug2006, Vol. 84 Issue 8, p1031 

    Regio- and stereo-selective Candida rugosa lipase (CRL)-catalyzed acetylations of (�)-syn-1-phenylbutan-1,3-diols ((�)-syn-1) generated two monoacetates, (+)-syn-2 and (�)-syn-3, whereas that of (�)-anti-1 produced a monoacetate, (+)-anti-3, and an unreacted (�)-anti-1.

  • Elucidation of Acyl Migration During Lipase-Catalyzed Production of Structured Phospholipids. Vikbjerg, Anders F.; Huiling Mu; Xuebing Xu // Journal of the American Oil Chemists' Society (JAOCS);Jul2006, Vol. 83 Issue 7, p609 

    Elucidation of acyl migration was carried out in the Lipozyme RM IM (Rhizomucor miehei)-catalyzed transesterification between soybean phosphatidylcholine (PC) and caprylic acid in solvent-free media. A five-factor response surface design was used to evaluate the influence of five major factors...

  • The role of acyl-coenzyme A carboxylase complex in lipstatin biosynthesis of Streptomyces toxytricini. Demirev, Atanas V.; Khanal, Anamika; Sedai, Bhishma R.; Si Kyu Lim; Min Kyun Na; Doo Hyun Nam // Applied Microbiology & Biotechnology;Jul2010, Vol. 87 Issue 3, p1129 

    Streptomyces toxytricini produces lipstatin, a specific inhibitor of pancreatic lipase, which is derived from two fatty acid moieties with eight and 14 carbon atoms. The pccB gene locus in 10.6 kb fragment of S. toxytricini chromosomal DNA contains three genes for acyl-coenzyme A carboxylase...

  • Kinetic Modeling and Analysis of Kinetic Parameters for Solvent-tolerant Lipase from Bacillus sphaericus MTCC 7542. Tamilarasan, K.; Kumar, M. Dharmendira // Research Journal of Microbiology;2011, Vol. 6 Issue 7, p575 

    Organic Solvents Tolerant (OST) lipases are required in biotechnological applications, especially in the production of biopolymer materials, biodiesel and in the synthesis of fine chemicals. In the present study, a kinetic model has been developed for the batch fermentation used for the...

  • Friedel-Craft Acylation of ar-Himachalene: Synthesis of Acyl-ar-Himachalene and a New Acyl-Hydroperoxide. Hossini, Issam; Harrad, Mohamed Anoir; Ali, Mustapha Ait; El Firdoussi, Larbi; Karim, Abdallah; Valerga, Pedro; Puerta, M. Carmen // Molecules;Jul2011, Vol. 16 Issue 7, p5886 

    Friedel-Craft acylation at 100 °C of 2,5,9,9-tetramethyl-6,7,8,9-tetrahydro-5H-benzocycloheptene [ar-himachalene (1)], a sesquiterpenic hydrocarbon obtained by catalytic dehydrogenation of α-, β- and γ-himachalenes, produces a mixture of two compounds:...

Share

Read the Article

Courtesy of THE LIBRARY OF VIRGINIA

Sorry, but this item is not currently available from your library.

Try another library?
Sign out of this library

Other Topics