Advanced
Fast Determination of Multiple-Reaction Intermediates for Long-Chain Dicarboxylic Acid Biotransformation by Gas Chromatography-Flame Ionization Detector
Fast Determination of Multiple-Reaction Intermediates for Long-Chain Dicarboxylic Acid Biotransformation by Gas Chromatography-Flame Ionization Detector
Journal of Microbiology and Biotechnology. 2015. May, 25(5): 704-708
Copyright © 2015, The Korean Society For Microbiology And Biotechnology
  • Received : February 11, 2015
  • Accepted : February 15, 2015
  • Published : May 28, 2015
Download
PDF
e-PUB
PubReader
PPT
Export by style
Article
Author
Metrics
Cited by
TagCloud
About the Authors
Yong-Han Cho
Department of Bio and Fermentation Convergence Technology, Kookmin University, Seoul 136-702, Republic of Korea
Hye-Jin Lee
Department of Bio and Fermentation Convergence Technology, Kookmin University, Seoul 136-702, Republic of Korea
Jung-Eun Lee
Department of Bio and Fermentation Convergence Technology, Kookmin University, Seoul 136-702, Republic of Korea
Soo-Jung Kim
Center for Food and Bioconvergence, Seoul National University, Seoul 151-921, Republic of Korea
Kyungmoon Park
Department of Bio and Chemical Engineering, Hongik University, Sejong 339-701, Republic of Korea
Do Yup Lee
Department of Bio and Fermentation Convergence Technology, Kookmin University, Seoul 136-702, Republic of Korea
ycpark@kookmin.ac.kr
Yong-Cheol Park
Department of Bio and Fermentation Convergence Technology, Kookmin University, Seoul 136-702, Republic of Korea
ycpark@kookmin.ac.kr

Abstract
For the analysis of multiple-reaction intermediates for long-chain dicarboxylic acid biotransformation, simple and reproducible methods of extraction and derivatization were developed on the basis of gas chromatography with flame ionization detector (GC-FID) instead of mass spectrometry. In the derivatization step, change of the ratio of pyridine to MSTFA from 1:3 to 9:1 resulted in higher peak intensity ( p = 0.021) and reproducibility (0.6%CV) when analyzing 32 g/l ricinoleic acid (RA). Extraction of RA and ω-hydroxyundec-9-enoic acid with water containing 100 mM Tween 80 showed 90.4-99.9% relative extraction efficiency and 2-7%CV compared with those with hydrophobic ethyl acetate. In conclusion, reduction of the pyridine content and change of the extraction solvent to water with Tween 80 provided compatible derivatization and extraction methods to GC-FID-based analysis of longchain carboxylic acids.
Keywords
PPT Slide
Lager Image
PPT Slide
Lager Image
PPT Slide
Lager Image
PPT Slide
Lager Image
PPT Slide
Lager Image
PPT Slide
Lager Image
Acknowledgements
This research was supported by the R&D Program of MOTIE/KEIT (10044647) and also by the National Research Foundation of Korea Grant (2013M1A2A2072603 and 2013R1A1A1058163) funded by the Ministry of Science, ICT and Future Planning and Technology. We thank Prof. Jin-Byung Park at Ewha Womans University for analyzing the samples with gas chromatography-mass spectrometry.
References
Bland JM , Altman DG 1996 Statistics notes: measurement error proportional to the mean. BMJ 313 106 -    DOI : 10.1136/bmj.313.7049.106
Dodds ED , McCoy MR , Rea LD , Kennish JM 2005 Gas chromatographic quantification of fatty acid methyl esters: flame ionization detection vs electron impact mass spectrometry. Lipids 40 419 - 428    DOI : 10.1007/s11745-006-1399-8
Fiehn O 2006 Metabolite profiling inArabidopsis. Methods Mol. Biol. 323 439 - 447
Franzmann C , Wächter J , Dittmer N , Humpf H-U 2010 Ricinoleic acid as a marker for ergot impurities in rye and rye products. J. Agric. Food Chem. 58 4223 - 4229    DOI : 10.1021/jf1006903
Hudson J , MacKenzie C , Joblin K 1995 Conversion of oleic acid to 10-hydroxystearic acid by two species of ruminal bacteria. Appl. Microbiol. Biotechnol. 44 1 - 6    DOI : 10.1007/BF00164472
Jeon E-Y , Lee J-H , Yang K-M , Joo Y-C , Oh D-K , Park J-B 2012 Bioprocess engineering to produce 10-hydroxystearic acid from oleic acid by recombinantEscherichia coliexpressing the oleate hydratase gene ofStenotrophomonas maltophilia. Process Biochem. 47 941 - 947    DOI : 10.1016/j.procbio.2012.03.002
Joo Y-C , Seo E-S , Kim Y-S , Kim K-R , Park J-B , Oh D-K 2012 Production of 10-hydroxystearic acid from oleic acid by whole cells of recombinantEscherichia colicontaining oleate hydratase fromStenotrophomonas maltophilia. J. Biotechnol. 158 17 - 23    DOI : 10.1016/j.jbiotec.2012.01.002
Köckritz A , Martin A 2011 Synthesis of azelaic acid from vegetable oil-based feedstocks. Eur. J. Lipid Sci. Technol. 113 83 - 91    DOI : 10.1002/ejlt.201000117
Kim K-R , Seo M-H , Park J-B , Oh D-K 2014 Stereospecific production of 9R-hydroxy-10E, 12Z-octadecadienoic acid from linoleic acid by recombinantEscherichia colicells expressing 9R-lipoxygenase fromNostocsp. SAG 25.82. J. Mol. Catal. B Enzym. 104 56 - 63    DOI : 10.1016/j.molcatb.2014.03.009
Kim K , Kim S-K , Park Y-C , Seo J-H 2014 Enhanced production of 3-hydroxypropionic acid from glycerol by modulation of glycerol metabolism in recombinantEscherichia coli. Bioresour. Technol. 156 170 - 175    DOI : 10.1016/j.biortech.2014.01.009
Kim S , Lee DY , Wohlgemuth G , Park HS , Fiehn O , Kim KH 2013 Evaluation and optimization of metabolome sample preparation methods forSaccharomyces cerevisiae. Anal. Chem. 85 2169 - 2176    DOI : 10.1021/ac302881e
Lee DY , Fiehn O 2008 High quality metabolomic data forChlamydomonas reinhardtii. Plant Methods 4 7 -    DOI : 10.1186/1746-4811-4-7
Lee SH , Oh HM , Jo BH , Lee SA , Shin SY , Kim HS 2014 Higher biomass productivity of microalgae in an attached growth system, using wastewater. J. Microbiol. Biotechnol. 24 1566 - 1573
Lee Y-A , Jeon E-Y , Lee S-M , Bornscheuer UT , Park J-B 2014 Engineering the substrate-binding domain of an esterase enhances its hydrolytic activity toward fatty acid esters. Process Biochem. 49 2101 - 2106    DOI : 10.1016/j.procbio.2014.09.019
Matuszewski B , Constanzer M , Chavez-Eng C 1998 Matrix effect in quantitative LC/MS/MS analyses of biological fluids: a method for determination of finasteride in human plasma at picogram per milliliter concentrations. Anal. Chem. 70 882 - 889    DOI : 10.1021/ac971078+
Shin MH , Lee DY , Liu K-H , Fiehn O , Kim KH 2010 Evaluation of sampling and extraction methodologies for the global metabolic profiling ofSaccharophagus degradans. Anal. Chem. 82 6660 - 6666    DOI : 10.1021/ac1012656
Song JW , Jeon EY , Song DH , Jang HY , Bornscheuer UT , Oh DK , Park JB 2013 Multistep enzymatic synthesis of longchain α, ω-dicarboxylic and ω-hydroxycarboxylic acids from renewable fatty acids and plant oils. Angew. Chem. Int. Ed. Engl. 52 2534 - 2537    DOI : 10.1002/anie.201209187
Souza KS , Schwan RF , Dias DR 2014 Lipid and citric acid production by wild yeasts grown in glycerol. J. Microbiol. Biotechnol. 24 497 - 506    DOI : 10.4014/jmb.1310.10084
Zhang F , Huang C , Xu T 2009 Production of sebacic acid using two-phase bipolar membrane electrodialysis. Ind. Eng. Chem. Res. 48 7482 - 7488    DOI : 10.1021/ie900485k