Abstract

A study of the proposed mechanism enantioselective esterification of chiral alcohols by lipase enzymes in organic solvents. Initially the esterification of synthetically useful chiral auxiliaries of the 8- phenylementhol type by commercially available Candida rugosa will be studied. Racemic trans-2-substituted cyclohexanols will be synthesized by expoxide ring opening of cyclohexene oxides. These alcohols will be resolved and the rate of esterification of each enantiomer with lipase will be measured. Kinetic constants will be correlated to computer-generated electrostatic parameters to construct a three dimensional model of the enzyme's active site with respect to theses alcohol substrates. Along with X-ray structures of the lipase, the model will be used to understand the mechanism of enantioselective esterification of alcohols by Candida rugosa lipase. The alcohols resolved in this work will be evaluated as chiral auxiliaries and incorporated into stationary phases to separate enantiomer by chiral- column HPLC. These activities are important to the synthesis of biologically active compounds.

  Funding Agency

Agency
National Institute of Health (NIH)
Institute
National Institute of General Medical Sciences (NIGMS)
Type
Minority Biomedical Research Support - MBRS (S06)
Project #
2S06GM008012-25
Application #
3734119
Study Section
Project Start
Project End
Budget Start
Budget End
Support Year
25
Fiscal Year
1995
Total Cost
Indirect Cost

  Institution

Name
University of Texas El Paso
Department
Type
DUNS #
City
El Paso
State
TX
Country
United States
Zip Code
79968

  Publications

Rocha-Gutiérrez, Beatriz A; Lee, Wen-Yee; Shane Walker, W (2016) Mass balance and mass loading of polybrominated diphenyl ethers (PBDEs) in a tertiary wastewater treatment plant using SBSE-TD-GC/MS. Water Sci Technol 73:302-8
Vargas-Medrano, Javier; Sierra-Fonseca, Jorge A; Plenge-Tellechea, Luis F (2016) 1,2-Dichlorobenzene affects the formation of the phosphoenzyme stage during the catalytic cycle of the Ca(2+)-ATPase from sarcoplasmic reticulum. BMC Biochem 17:5
Buhaya, Munir H; Galvan, Steven; Maldonado, Rosa A (2015) Incidence of Trypanosoma cruzi infection in triatomines collected at Indio Mountains Research Station. Acta Trop 150:97-9
Vasquez, Miguel A; Iniguez, Eva; Das, Umashankar et al. (2015) Evaluation of ?,?-unsaturated ketones as antileishmanial agents. Antimicrob Agents Chemother 59:3598-601
Dagda, Ruben K; Gasanov, Sardar E; Zhang, Boris et al. (2014) Molecular models of the Mojave rattlesnake (Crotalus scutulatus scutulatus) venom metalloproteinases reveal a structural basis for differences in hemorrhagic activities. J Biol Phys 40:193-216
Serna, Carylinda; Lara, Joshua A; Rodrigues, Silas P et al. (2014) A synthetic peptide from Trypanosoma cruzi mucin-like associated surface protein as candidate for a vaccine against Chagas disease. Vaccine 32:3525-32
Rodrigues, Marcio L; Nakayasu, Ernesto S; Almeida, Igor C et al. (2014) The impact of proteomics on the understanding of functions and biogenesis of fungal extracellular vesicles. J Proteomics 97:177-86
Nagy, Zsuzsanna S; Ross, Jeremy A; Rodriguez, Georgialina et al. (2013) Genome wide mapping reveals PDE4B as an IL-2 induced STAT5 target gene in activated human PBMCs and lymphoid cancer cells. PLoS One 8:e57326
Rico-Martínez, Roberto; Walsh, Elizabeth J (2013) Sexual Reproductive Biology of a Colonial Rotifer Sinantherina socialis (Rotifera: Monogononta): Do mating strategies vary between colonial and solitary rotifer species? Mar Freshw Behav Physiol 46:419-430
Jin, Seoweon; Staniswalis, Joan G; Mallawaarachchi, Indika (2013) Principal Differential Analysis with a Continuous Covariate: Low Dimensional Approximations for Functional Data. J Stat Comput Simul 83:

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