Biosynthesis of Flavour-Active Esters via Lipase-Mediated Reactions and Mechanisms
Jingcan Sun A , Liang Wei Wilson Lee A and Shao Quan Liu A B C
+ Author Affiliations
- Author Affiliations
A Food Science and Technology Programme, Department of Chemistry, National University of Singapore, Science Drive 3, Singapore 117543.
B National University of Singapore (Suzhou) Research Institute, No. 377 Linquan Street, Suzhou Industrial Park, Suzhou, Jiangsu 215123, China.
C Corresponding author. Email: chmLsq@nus.edu.sg
Ms Jingcan Sun obtained her Master's degree in biochemical engineering from the Chinese Academy of Sciences in 2009. She then continued with her Ph.D. studies in the Food Science and Technology Programme at the National University of Singapore, and received her Ph.D. degree in 2014. She currently works at Nestle R&D, Singapore. |
Mr Liang Wei Wilson Lee received his B.Sc. (with honours) in chemistry and biological chemistry from Nanyang Technological University of Singapore. He is currently a Ph.D. student at the National University of Singapore, working on the fungal fermentation of green coffee beans. |
Dr Shao Quan Liu obtained his Ph.D. degree from Massey University, New Zealand, in 1994. He is currently an associate professor in the Food Science and Technology Programme, Department of Chemistry, National University of Singapore. He teaches food fermentation and flavour science, and conducts research in the same areas. |
Australian Journal of Chemistry 67(10) 1373-1381 https://doi.org/10.1071/CH14225
Submitted: 9 April 2014 Accepted: 29 May 2014 Published: 16 July 2014
Abstract
Flavour active esters belong to one group of fine aroma chemicals that impart desirable fruity flavour notes and are widely applied in the flavour and fragrance industry. Due to the increasing consumer concern about health, natural products are attracting more attention than chemically synthesized substances. The biosynthesis of flavour-active esters via lipase-catalyzed reactions is one of the most important biotechnological methods for natural flavour generation. To proceed with the industrial production of esters on a large scale, it is critical to understand the enzyme properties and behaviours under different reaction conditions. In this short review, the lipase-catalyzed reactions in various systems and their mechanisms for synthesis of the esters are summarized and discussed.
References
[1] K. Touhara, in The Senses: A Comprehensive Reference (Eds A. I. Basbaum, A. Kaneko, G. M. Shepherd, G. Westheimer, T. D. Albright, R. H. Masland, P. Dallos, D. Oertel, S. Firestein, G. K. Beauchamp, M. C. Bushnell, J. H. Kaas, E. Gardner) 2008, Vol. 4, pp. 527–544 (Academic Press: New York, NY).[2] K. J. Verstrepen, G. Derdelinckx, J. P. Dufour, J. Winderickx, J. M. Thevelein, I. S. Pretorius, F. R. Delvaux, J. Biosci. Bioeng. 2003, 96, 110.
| Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DC%2BD3sXotF2jurc%3D&md5=8571c53faadf27aef53ce2758f2e3fdfCAS | 16233495PubMed |
[3] S. Serra, C. Fuganti, E. Brenna, Trends Biotechnol. 2005, 23, 193.
| Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DC%2BD2MXisVWku7o%3D&md5=f50b0f3023bc29587bec3d19ae4e4806CAS | 15780711PubMed |
[4] M. Montero-Calderón, M. A. Rojas-Graü, O. Martín-Belloso, J. Food Sci. 2010, 75, S506.
| Crossref | GoogleScholarGoogle Scholar | 21535624PubMed |
[5] M. C. Gonzalez-Mas, J. L. Rambla, M. C. Alamar, A. Gutierrez, A. Granell, PLoS ONE 2011, 6, e22016.
| Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DC%2BC3MXhtVehtLzI&md5=4301219044af69a39aed31df62eab40fCAS | 21818287PubMed |
[6] M. Longo, M. Sanromán, Food Technol. Biotechnol. 2006, 44, 335.
| 1:CAS:528:DC%2BD28XhtFSktbzM&md5=afc10e82adc226d53aa6273531b3d9ffCAS |
[7] I. L. Gatfield, Perfum. Flavor. 1995, 20, 5.
| 1:CAS:528:DyaK2MXpt1ykurw%3D&md5=6a6da558cf10e9d10e3680f7c1e7ddd3CAS |
[8] R. G. Berger, U. Krings, H. Zorn, in Food Flavour Technology (Eds A. J. Taylor, R. Linforth) 2002, pp. 60–100 (Wiley-Blackwell: Oxford).
[9] E. J. Vandamme, W. Soetaert, J. Chem. Technol. Biotechnol. 2002, 77, 1323.
| Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DC%2BD38XpsVOnuro%3D&md5=37af778e4b87b4bba443cc4b03dd13aeCAS |
[10] D. Hua, P. Xu, Biotechnol. Adv. 2011, 29, 654.
| Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DC%2BC3MXht1Kktb3E&md5=59ed1f3aed4f9cd8463cc0c69b530c3dCAS | 21601630PubMed |
[11] U. Krings, R. Berger, Appl. Microbiol. Biotechnol. 1998, 49, 1.
| Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DyaK1cXhtVantLY%3D&md5=db3fd72175ae11ad340ca901c1a6c5ffCAS | 9487704PubMed |
[12] H. Chahiniana, L. Sarda, Protein Pept. Lett. 2009, 16, 1149.
| Crossref | GoogleScholarGoogle Scholar |
[13] E. Alvarez-Macarie, J. Baratti, J. Mol. Catal. B – Enzym. 2000, 10, 377.
| Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DC%2BD3cXltlWgtr4%3D&md5=bd9d77ca9954755eac3ff7d32ecbd64dCAS |
[14] S.-Q. Liu, K. Baker, M. Bennett, R. Holland, G. Norris, V. Crow, Int. Dairy J. 2004, 14, 865.
| Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DC%2BD2cXmsVCqur4%3D&md5=dedb0bd4dd1031304d4c6f47709db5b3CAS |
[15] S. Torres, M. D. Baigorí, S. Swathy, A. Pandey, G. R. Castro, Food Res. Int. 2009, 42, 454.
| Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DC%2BD1MXkslKmsbw%3D&md5=66035ec037c54e9e8346edd5ba598973CAS |
[16] K.-E. Jaeger, M. T. Reetz, Trends Biotechnol. 1998, 16, 396.
| Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DyaK1cXls1Ontrw%3D&md5=414b298d15b31152bda26f6c5be50081CAS | 9744114PubMed |
[17] K. Holwerda, P. E. Verkade, A. H. A de Willigen, Recl. Trav. Chim. Pay.-B. 1936, 55, 43.
| Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DyaA28XhvFKntw%3D%3D&md5=a568107f023363f7e2c7e5293d640d98CAS |
[18] F. Schønheyder, K. Volqvartz, Acta Physiol. Scand. 1945, 9, 57.
| Crossref | GoogleScholarGoogle Scholar |
[19] R. Verger, Trends Biotechnol. 1997, 15, 32.
| Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DyaK2sXhtFCiu7c%3D&md5=b8f51918a0e691930f0fb775363224d5CAS |
[20] Y. Bourne, C. Martinez, B. Kerfelec, D. Lombardo, C. Chapus, C. Cambillau, J. Mol. Biol. 1994, 238, 709.
| Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DyaK2cXltVaqur0%3D&md5=f1786bab98284f43528627f12c99050aCAS | 8182745PubMed |
[21] D. Lang, B. Hofmann, L. Haalck, H.-J. Hecht, F. Spener, R. D. Schmid, D. Schomburg, J. Mol. Biol. 1996, 259, 704.
| Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DyaK28XjvFahtrk%3D&md5=64905c19016cc8f8629095501054083dCAS | 8683577PubMed |
[22] G. De Simone, V. Menchise, V. Alterio, L. Mandrich, M. Rossi, G. Manco, C. Pedone, J. Mol. Biol. 2004, 343, 137.
| Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DC%2BD2cXnslKqtbs%3D&md5=2cdc7b82be8313773294f44ee8e8f683CAS | 15381425PubMed |
[23] J. M. Mancheño, M. A. A. Pernas, M. A. J. Martínez, B. Ochoa, M. L. Rúa, J. A. Hermoso, J. Mol. Biol. 2003, 332, 1059.
| Crossref | GoogleScholarGoogle Scholar | 14499609PubMed |
[24] J. D. A. Tyndall, S. Sinchaikul, L. A. Fothergill-Gilmore, P. Taylor, M. D. Walkinshaw, J. Mol. Biol. 2002, 323, 859.
| Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DC%2BD38Xot1Knu7c%3D&md5=c19dcb2415abc1ccf70c1f737174ddb6CAS |
[25] G. van Pouderoyen, T. Eggert, K.-E. Jaeger, B. W. Dijkstra, J. Mol. Biol. 2001, 309, 215.
| Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DC%2BD3MXjsF2lu7o%3D&md5=fd2d0ae2f4081f6321e52a7e676bf6dcCAS | 11491291PubMed |
[26] R. Fernandez-Lafuente, J. Mol. Catal. B – Enzym. 2010, 62, 197.
| Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DC%2BC3cXnt1Wquw%3D%3D&md5=e59fc6e2b27a2e3f96693a1b32673a82CAS |
[27] R. C. Rodrigues, R. Fernandez-Lafuente, J. Mol. Catal. B – Enzym. 2010, 66, 15.
| Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DC%2BC3cXovFylsb8%3D&md5=76849184a0e7d95986a0bcba2d70c80dCAS |
[28] U. Derewenda, A. M. Brzozowski, D. M. Lawson, Z. S. Derewenda, Biochemistry 1992, 31, 1532.
| Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DyaK38XnvFaqsw%3D%3D&md5=0e7eb38661b7abcf43189b6540d23011CAS | 1737010PubMed |
[29] J. D. Weete, O.-M. Lai, C. C. Akoh, in Food Lipids: Chemistry, Nutrition, and Biotechnology (Eds C. C. Akoh, D. B. Min) 2008, pp. 779–789 (CRC Press/Taylor & Francis Group: Boca Raton, FL).
[30] M. Cygler, P. Grochulski, J. D. Schrag, Can. J. Microbiol. 1995, 41, 289.
| Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DyaK2MXmsFyqsr0%3D&md5=950c2a0382378ea64ac27e06d875329eCAS | 7606666PubMed |
[31] L. B. Fomuso, C. C. Akoh, Food Res. Int. 2002, 35, 15.
| Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DC%2BD38XovFaksA%3D%3D&md5=c7a8effc58cd85fe770b3b5ea7f3572bCAS |
[32] F. D. Gunstone, J. Sci. Food Agric. 1999, 79, 1535.
| Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DyaK1MXmt1Wjs7c%3D&md5=5a7ad433d0b4bb25a1cd2bb13da3261fCAS |
[33] K.-E. Jaeger, T. Eggert, Curr. Opin. Biotechnol. 2002, 13, 390.
| Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DC%2BD38XmsFOnsb8%3D&md5=1bed48274137d09f5ab9f158dcc0ae32CAS | 12323363PubMed |
[34] F. Hasan, A. A. Shah, A. Hameed, Enzyme Microb. Technol. 2006, 39, 235.
| Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DC%2BD28XkslSksbc%3D&md5=776533709ece3a143aa3b3ad350c75f2CAS |
[35] R. C. Rodrigues, G. Volpato, K. Wada, M. A. Z. Ayub, J. Am. Oil Chem. Soc. 2008, 85, 925.
| Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DC%2BD1cXhtFSmsLzN&md5=e2ee227b5f87d20e1e6509d1b9fcd9e6CAS |
[36] P. Adhikari, J. A. Shin, J. H. Lee, H. R. Kim, I. H. Kim, S. T. Hong, K. T. Lee, Food Bioprocess Tech. 2012, 5, 2474.
| Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DC%2BC38XhtVOgsbvM&md5=2c4b903ef77baec83b0adaed58ef544dCAS |
[37] V. Dossat, D. Combes, A. Marty, Enzyme Microb. Technol. 2002, 30, 90.
| Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DC%2BD38Xit1Kq&md5=a3d195b647df7cfd1a1d220f2ba92a8aCAS |
[38] N. Li, H. Wu, M. Zong, W. Lou, Chin. J. Catal. 2007, 28, 333.
[39] Y. Zheng, J. Quan, X. Ning, L. M. Zhu, B. Jiang, Z. Y. He, World J. Microbiol. Biotechnol. 2009, 25, 41.
| Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DC%2BD1cXhsVKjt77L&md5=1e4db3c212c8f985b011df90c94dae7fCAS |
[40] F. Ma, L. D. Clements, M. A. Hanna, Ind. Eng. Chem. Res. 1998, 37, 3768.
| Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DyaK1cXltVWmtL0%3D&md5=7ce80e45a44fc30ec07527bf7118c873CAS |
[41] G. M. Tashtoush, M. I. Al-Widyan, M. M. Al-Jarrah, Energy Convers. Manage. 2004, 45, 2697.
| Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DC%2BD2cXltFWgsbg%3D&md5=9a3c42f00c4474135bca34d133cfa2b8CAS |
[42] F. A. M. Shaharin, J. Biotechnol. 2008, 136, S357.
[43] H. Shekarchizadeh, M. Kadivar, Food Chem. 2012, 135, 155.
| Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DC%2BC38XmvFKgu7c%3D&md5=de0eda4a2f33cae8fc0cfbec60019dcfCAS |
[44] N. Sahin, C. C. Akoh, A. Karaali, J. Agric. Food Chem. 2005, 53, 5779.
| Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DC%2BD2MXltlarsLg%3D&md5=233b4e95390c5b0d96bbe7370d81e140CAS | 15998148PubMed |
[45] T. Yang, X. Xu, C. He, L. Li, Food Chem. 2003, 80, 473.
| Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DC%2BD3sXosVyqsA%3D%3D&md5=a462540d74a6d97c3216ba7139d6efa6CAS |
[46] R. Gupta, P. Rathi, S. Bradoo, Crit. Rev. Food Sci. Nutr. 2003, 43, 635.
| Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DC%2BD2cXpsFeh&md5=aa210af32611f0a0ff176bc178ec353bCAS | 14669881PubMed |
[47] M. A. Regado, B. M. Cristóvao, C. G. Moutinho, V. M. Balcao, R. Aires-Barros, J. P. M. Ferreira, F. Xavier Malcata, Int. J. Food Sci. Technol. 2007, 42, 961.
| Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DC%2BD2sXptVyjur8%3D&md5=6139de00004bf5a1d19cb7773a62bec7CAS |
[48] V. M. Balcao, F. X. Malcata, Biotechnol. Adv. 1998, 16, 309.
| Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DyaK1cXit1aqsrk%3D&md5=0a0b3a8f1adbb9e988b530228ea4f0d2CAS | 14538148PubMed |
[49] A. Rajendran, I. A. Palanisamy, V. Thangavelu, Braz. Arch. Biol. Technol. 2009, 52, 207.
| Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DC%2BD1MXkvVWrsL0%3D&md5=e4aa7c806cc9e41d178bcd4043c2bb63CAS |
[50] H. de Castro, P. De Oliveira, E. Pereira, Biotechnol. Lett. 1997, 19, 229.
| Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DyaK2sXisVWhtrs%3D&md5=b30c426d01c81bb34c1689c5d5f13cd3CAS |
[51] A. Güvenç, N. Kapucu, H. Kapucu, Ö. Aydoğan, Ü. Mehmetoğlu, Enzyme Microb. Technol. 2007, 40, 778.
| Crossref | GoogleScholarGoogle Scholar |
[52] A. Güvenç, N. Kapucu, Ü. Mehmetoğlu, Process Biochem. 2002, 38, 379.
| Crossref | GoogleScholarGoogle Scholar |
[53] S. Hari Krishna, S. Divakar, S. G. Prapulla, N. G. Karanth, J. Biotechnol. 2001, 87, 193.
| Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DC%2BD3MXjtFCrtbc%3D&md5=a5fdcef91dc1ced43bbfe6f97b341980CAS | 11334663PubMed |
[54] G. Ozyilmaz, E. Gezer, J. Mol. Catal. B – Enzym. 2010, 64, 140.
| Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DC%2BC3cXmtFCnt7o%3D&md5=8ce0543848866b1bbce49e37d0ebb98fCAS |
[55] M. Romero, L. Calvo, C. Alba, M. Habulin, M. Primožič, Ž. Knez, J. Supercrit. Fluids 2005, 33, 77.
| Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DC%2BD2cXpt1Wkurg%3D&md5=e8b9faecadb5e47a92c1a73186f7e570CAS |
[56] J.-P. Chen, J. Ferment. Bioeng. 1996, 82, 404.
| Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DyaK28XmvFaitb8%3D&md5=f551c7bd9c49ccba14dc3d2a106b7adeCAS |
[57] M. Karra-Châabouni, S. Pulvin, D. Touraud, D. Thomas, Biotechnol. Lett. 1996, 18, 1083.
| Crossref | GoogleScholarGoogle Scholar |
[58] P. Pires-Cabral, M. da Fonseca, S. Ferreira-Dias, Biochem. Eng. J. 2007, 33, 148.
| Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DC%2BD2sXhtleit7Y%3D&md5=83643363689590b3b04d25db97891389CAS |
[59] T. Raghavendra, D. Sayania, D. Madamwar, J. Mol. Catal. B – Enzym. 2010, 63, 31.
| Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DC%2BC3cXht12qur0%3D&md5=51da9491d127f93947b55398c017b085CAS |
[60] Y. Xu, D. Wang, X. Q. Mu, G. A. Zhao, K. C. Zhang, J. Mol. Catal. B – Enzym. 2002, 18, 29.
| Crossref | GoogleScholarGoogle Scholar |
[61] S. Huang, H. Chang, M. Goto, Enzyme Microb. Technol. 1998, 22, 552.
| Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DyaK1cXjs1egsr0%3D&md5=59c4c8e27d6f0571ab9ba0a72ce17974CAS |
[62] L. Gubicza, A. Kabiri-Badr, E. Keoves, K. Belafi-Bako, J. Biotechnol. 2000, 84, 193.
| Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DC%2BD3cXot12ksrw%3D&md5=b8a57c83069cd72e11e2ccffbd47e4e2CAS |
[63] J. Giacometti, F. Giacometti, Č. Milin, Đ. A. Vasić-Rački, J. Mol. Catal. B – Enzym. 2001, 11, 921.
| Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DC%2BD3MXptlWntg%3D%3D&md5=753ed30de66bfb1af2fa32944cb44710CAS |
[64] J. J. Jafar, P. M. Budd, R. Hughes, J. Membr. Sci. 2002, 199, 117.
| Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DC%2BD38XhtFGqt70%3D&md5=3ec003b55fe51492806553283b3b33bdCAS |
[65] S. J. Kwon, K. M. Song, W. H. Hong, J. S. Rhee, Biotechnol. Bioeng. 1995, 46, 393.
| Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DyaK2MXlt1Wks7c%3D&md5=70f1b8f88045504cbd5c91e3d4725217CAS | 18623327PubMed |
[66] P. Mahapatra, A. Kumari, V. Kumar Garlapati, R. Banerjee, A. Nag, J. Mol. Catal. B – Enzym. 2009, 60, 57.
| Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DC%2BD1MXms1Oju74%3D&md5=88167850fb694d315d6f73ec7faaad40CAS |
[67] T. Chatterjee, D. Bhattacharyya, J. Am. Oil Chem. Soc. 1998, 75, 651.
| Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DyaK1cXjt1CgsLs%3D&md5=124bb9ed2f447c9ecb71c9154a20e166CAS |
[68] A. Güvenç, N. Kapucu, E. Bayraktar, Ü. Mehmetoğlu, Chem. Eng. Commun. 2003, 190, 948.
| Crossref | GoogleScholarGoogle Scholar |
[69] M. A. Bezerra, R. E. Santelli, E. P. Oliveira, L. S. Villar, L. A. Escaleira, Talanta 2008, 76, 965.
| Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DC%2BD1cXhtVOmtbvN&md5=ef3fdb7de57720043617e10d90e233d7CAS | 18761143PubMed |
[70] P. Mahapatra, A. Kumari, V. Kumar Garlapati, R. Banerjee, A. Nag, J. Mol. Catal. B – Enzym. 2009, 60, 57.
| Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DC%2BD1MXms1Oju74%3D&md5=88167850fb694d315d6f73ec7faaad40CAS |
[71] G. Macedo, G. Pastore, M. Rodrigues, Process Biochem. 2004, 39, 687.
| Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DC%2BD2cXhslCjur0%3D&md5=bd39218683e67b85c971a12042240900CAS |
[72] R. Ben Salah, H. Ghamghui, N. Miled, H. Mejdoub, Y. Gargouri, J. Biosci. Bioeng. 2007, 103, 368.
| Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DC%2BD2sXmslOqtrY%3D&md5=d892e6590e4d06e1026a76f566ee5b63CAS | 17502279PubMed |
[73] G. Langrand, N. Rondot, C. Triantaphylides, J. Baratti, Biotechnol. Lett. 1990, 12, 581.
| Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DyaK3MXkvVSl&md5=85524f7cfdf4b11e369df1e7e85f2ddaCAS |
[74] C. Li, J. Sun, C. Fu, B. Yu, S.-Q. Liu, T. Li, D. Huang, Food Chem. 2014, 145, 796.
| Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DC%2BC3sXhs1WhtL%2FI&md5=be4db606246c0a6dc61e86eca274762eCAS | 24128547PubMed |
[75] J. Sun, J. H. Chin, W. Zhou, B. Yu, P. Curran, S.-Q. Liu, J. Am. Oil Chem. Soc. 2012, 89, 1991.
| Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DC%2BC38XhsFCltrvF&md5=10dd5474443e20e8e01f15cc485fcb02CAS |
[76] J. Sun, B. Yu, P. Curran, S.-Q. Liu, Food Chem. 2012, 134, 89.
| Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DC%2BC38Xjs1Wntbo%3D&md5=4d633ead7aacf3fe6aed360cc84d5764CAS |
[77] C. Li, J. Sun, T. Li, S.-Q. Liu, D. Huang, Food Chem. 2014, 154, 205.
| Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DC%2BC2cXitFansbs%3D&md5=efe3646a51ea9f8a690636de870ab724CAS | 24518334PubMed |
[78] A. M. Klibanov, Nature 2001, 409, 241.
| Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DC%2BD3MXlvFWiuw%3D%3D&md5=f82d3488e581cdaae9263e42e27095f4CAS | 11196652PubMed |
[79] M. Karra-Châabouni, H. Ghamgui, S. Bezzine, A. Rekik, Y. Gargouri, Process Biochem. 2006, 41, 1692.
| Crossref | GoogleScholarGoogle Scholar |
[80] P. A. Claon, C. C. Akoh, Enzyme Microb. Technol. 1994, 16, 835.
| Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DyaK2MXps1Shtg%3D%3D&md5=179c361c2b5039b2fdb4adabeda864e1CAS |
[81] W. Chulalaksananukul, J.-S. Condoret, D. Combes, Enzyme Microb. Technol. 1992, 14, 293.
| Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DyaK38XhslCnt7g%3D&md5=5f42b9240469105acf0f5dddbe373d66CAS |
[82] S.-W. Chang, J.-F. Shaw, C.-H. Shieh, C.-J. Shieh, J. Agric. Food Chem. 2006, 54, 7125.
| Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DC%2BD28Xoslals78%3D&md5=9ef90287c0baf21ba0de17681c41d28fCAS | 16968072PubMed |
[83] S. V. Dzyuba, R. A. Bartsch, Angew. Chem. Int. Ed. 2003, 42, 148.
| Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DC%2BD3sXos1amuw%3D%3D&md5=fe9338667377be64119eb405b3aa684eCAS |
[84] R. Sheldon, Chem. Comm. 2001, 23, 2399.
| Crossref | GoogleScholarGoogle Scholar | 12239988PubMed |
[85] E. Fehér, V. Illeová, I. Kelemen-Horváth, K. Bélafi-Bakó, M. Polakovič, L. Gubicza, J. Mol. Catal. B – Enzym. 2008, 50, 28.
| Crossref | GoogleScholarGoogle Scholar |
[86] M. Cvjetko, J. Vorkapić-Furač, P. Žnidaršič-Plazl, Process Biochem. 2012, 47, 1344.
| Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DC%2BC38Xns1Cjtr0%3D&md5=4be3120a0ff49ecf3865aafe363f11e6CAS |
[87] E. Fehér, B. Major, K. Bélafi-Bakó, L. Gubicza, Desalination 2009, 241, 8.
| Crossref | GoogleScholarGoogle Scholar |
[88] Y. Fan, J. Qian, J. Mol. Catal. B – Enzym. 2010, 66, 1.
| Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DC%2BC3cXovFylsL8%3D&md5=6254d1b3d21a54da5b7587246bc2021dCAS |
[89] A. Pohar, I. Plazl, P. Žnidaršič-Plazl, Lab Chip 2009, 9, 3385.
| Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DC%2BD1MXhtl2ksbzE&md5=e34b8bd964dd9750e5b27ac155b19ca3CAS | 19904405PubMed |
[90] Ž. Knez, J. Supercrit. Fluids 2009, 47, 357.
| Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DC%2BD1MXptlyrtA%3D%3D&md5=c56ef9a427dfbd1bac995dbda6de276cCAS |
[91] T. W. Randolph, H. Blanch, J. Prausnitz, C. Wilke, Biotechnol. Lett. 1985, 7, 325.
| Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DyaL2MXksFSnsbw%3D&md5=4d99dac61a4a0f1bf4ed7521b39ba9a3CAS |
[92] R. Kumar, J. Modak, G. Madras, Biochem. Eng. J. 2005, 23, 199.
| Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DC%2BD2MXis1Knsbk%3D&md5=92607e94af2657d35d06a338b8f4f605CAS |
[93] M. Habulin, S. Šabeder, M. A. Sampedro, Ž. Knez, Biochem. Eng. J. 2008, 42, 6.
| Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DC%2BD1cXhtVKiurzI&md5=4c315c6f0ae456a66f2a61bfdbdf365dCAS |
[94] M. Habulin, Ž. Knez, J. Chem. Technol. Biotechnol. 2001, 76, 1260.
| Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DC%2BD3MXptVKhtrk%3D&md5=46b4a90e76c98fe0d084b82c10764d32CAS |
[95] H. Ishikawa, M. Shimoda, A. Yonekura, Y. Osajima, J. Agric. Food Chem. 1996, 44, 2646.
| Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DyaK28Xlt1eqt74%3D&md5=042a0c7426b4d655f8ba41bcbe090430CAS |
[96] H. Monhemi, M. R. Housaindokht, M. R. Bozorgmehr, M. S. S. Googheri, J. Supercrit. Fluids 2012, 69, 1.
| Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DC%2BC38XhtVeqtbfO&md5=575c7c33d40160b967da3b07471122faCAS |
[97] D. Briand, E. Dubreucq, P. Galzy, Biotechnol. Lett. 1994, 16, 813.
| Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DyaK2MXpsVWltQ%3D%3D&md5=0402c72362229c47ee8e7380cbb1bc9dCAS |
[98] C. Lecointe, E. Dubreucq, P. Galzy, Biotechnol. Lett. 1996, 18, 869.
| Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DyaK28XltFGqsbw%3D&md5=9326e545e82df511013eb497a2aaa2c9CAS |
[99] L. Vaysse, A. Ly, G. Moulin, E. Dubreucq, Enzyme Microb. Technol. 2002, 31, 648.
| Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DC%2BD38XmvVCksbs%3D&md5=6a2be067bbce16cdcffacd642d93dd3dCAS |
[100] O. Boutur, E. Dubreucq, P. Galzy, Biotechnol. Lett. 1994, 16, 1179.
| Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DyaK2MXislWqs7o%3D&md5=4ab731e68fbc51821b3f0fa7b559d32bCAS |
[101] D. Briand, E. Dubreucq, P. Galzy, Eur. J. Biochem. 1995, 228, 169.
| Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DyaK2MXjvFKksbg%3D&md5=33df26904ddb7578e508529aca84b77cCAS | 7883000PubMed |
[102] J. Sun, B. Yu, P. Curran, S.-Q. Liu, Food Chem. 2012, 135, 2714.
| Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DC%2BC38Xhtlakt7jL&md5=02ea9f2ec52939cf9a923811455a48c7CAS | 22980863PubMed |
[103] B. Cheirsilp, A. H-Kittikun, S. Limkatanyu, Biochem. Eng. J. 2008, 42, 261.
| Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DC%2BD1cXhtFektrvI&md5=c9c636bf8e6ea27105389aa134bc5a28CAS |
[104] J. Sun, B. Yu, P. Curran, S.-Q. Liu, Food Chem. 2013, 141, 2828.
| Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DC%2BC3sXhtFWrs7bM&md5=bb08629aaf0b7e6f0e934e274d5ed72fCAS | 23871030PubMed |
[105] A. Tuerkan, S. Kalay, Turk. J. Biochem. 2008, 33, 45.
[106] G. D. Yadav, P. S. Lathi, Biochem. Eng. J. 2003, 16, 245.
| Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DC%2BD3sXotVyrtrw%3D&md5=58e20c2a36e12b135c3dc8176172796fCAS |
[107] G. D. Yadav, A. H. Trivedi, Enzyme Microb. Technol. 2003, 32, 783.
| Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DC%2BD3sXktFGmtbY%3D&md5=8a76a010f56ab72921784e08666ff68bCAS |
[108] S. Al-Zuhair, F. W. Ling, L. S. Jun, Process Biochem. 2007, 42, 951.
| Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DC%2BD2sXlt1aku7o%3D&md5=4f2d0ca80f96882b78322c18ac78ab90CAS |
[109] M. Rizzi, P. Stylos, A. Riek, M. Reuss, Enzyme Microb. Technol. 1992, 14, 709.
| Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DyaK3sXlsFSrtQ%3D%3D&md5=a4119fd5e0eed2181ab5a38bb8bda963CAS | 1368893PubMed |
[110] M. V. Oliveira, S. F. Rebocho, A. S. Ribeiro, E. A. Macedo, J. M. Loureiro, J. Supercrit. Fluids 2009, 50, 138.
| Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DC%2BD1MXotF2gsb4%3D&md5=2b63415fac36f76a27a91090fc6707deCAS |
