生物催化法生产2-苯乙醇的研究现状
The Study of Biotechnological Production of 2-Phenylethanol
DOI: 10.12677/bp.2012.22015, PDF, HTML, XML, 下载: 4,137  浏览: 17,877  科研立项经费支持
作者: 曹明乐, 黄 峰：山东大学微生物技术国家重点实验室，济南 ；姜兴林, 张海波, 咸 漠：中国科学院青岛生物能源与过程研究所，青岛
关键词: 2-苯乙醇；香料；生物催化；艾利氏途径；原位萃取；2-Phenylethanol; Spices; Bio-Catalytic; Ehrlich Pathway; ISPR
摘要: 2-苯乙醇(2-Phenylethanol)也叫β-苯乙醇，英文简称2-PE，具有淡雅、细腻、持久、玫瑰香味的芳香族香气物质。2-苯乙醇可以作为香料广泛应用于香水、化妆品、食品等行业，此外2-苯乙醇在医药中间体及精细化工等行业也有重要的开发价值。目前2-苯乙醇主要是通过化学方法合成，生物催化法具有能耗低、环境污染小及人们对“天然”产品的要求也越来越高使得生物催化法来合成“天然”的2-苯乙醇受到越来越多的重视。本综述主要介绍了2-苯乙醇的合成现状，并且着重对生物合成方法、代谢途径及当前发酵方法优缺点进行了论述。
Abstract: 2-Phenylethanol (β-Phenylethanol) is aromatic flavour and fragrance compound with an elegant, fine, endure, rose-like odour. It can be used as additives in perfume, cosmetic, food industries. It also can be used as pharmaceutical intermediates and fine chemicals. So far, 2-PE is mainly produced chemically. The biosynthesis of 2-PE is receiving more attentions, because of its low energy consumption, environmentally friendly, and the demand for the “natural” 2-PE. This review introduces the production of 2-PE especially the biosynthesis method, metabolic pathway, and fermentation method.
文章引用：曹明乐, 姜兴林, 张海波, 咸漠, 黄峰. 生物催化法生产2-苯乙醇的研究现状[J]. 生物过程, 2012, 2(2): 89-97. http://dx.doi.org/10.12677/bp.2012.22015

参考文献

[1] M. M. Etschmann, et al. Biotechnological production of 2-phenyl- ethanol. Applied Microbiology and Biotechnology, 2002, 59(1): 1-8.
[2] 杨晓, 陈芳, 李景明. 植物中2-苯乙醇的合成研究进展[J]. 园艺学报, 2010, 37: 1690-1694.
[3] K. Rusanov, et al. Microsatellite analysis of Rosa damascena Mill. Accessions reveals genetic similarity between genotypes used for rose oil production and old Damask rose varieties. TAG Theoretical and Applied Genetics, 2005, 111(4): 804-809.
[4] C. E. Fabre, P. J. Blanc and G. Goma. Production of 2-phenyl- ethyl alcohol by Kluyveromyces marxianus. Biotechnology Progress, 1998, 14(2): 270-274.
[5] G. S. Clark. Phenethyl alcohol. Perfum Flavor, 1990, 15: 37-44.
[6] US Food and Drug Administration. 2001 in Code of Federal Regulations 21CFR101.22, 2001.
[7] J. Schrader, et al. Applied biocatalysis for the synthesis of natural flavour compounds—Current industrial processes and future prospects. Biotechnology Letters, 2004, 26(6): 463-472.
[8] K. Yamaguchi, K. Ebitani and K. Kaneda. Hydrotalcite-cata- lyzed epoxidation of olefins using hydrogen peroxide and amide compounds. The Journal of Organic Chemistry, 1999, 64(8): 2966- 2968.
[9] P. Bedoukian. Phenylethyl alcohol. Perfumery and flavoring synthetics. Wheaton: Allured, 1986: 370-383.
[10] I. Kirm, et al. Hydrogenation of styrene oxide in the presence of supported platinum catalysts to produce 2-phenylethanol. Journal of Molecular Catalysis A: Chemical, 2007, 261(1): 98-103.
[11] 2008年1月世界香料精油类产品市场报告[J]. 国内外香化信息, 2008, 23(2): 1-3.
[12] J. Y. Hwang, et al. Simultaneous synthesis of 2-phenylethanol and L-homophenylalanine using aromatic transaminase with yeast Ehrlich pathway. Biotechnology and Bioengineering, 2009, 102(5): 1323-1329.
[13] Z. Yang, et al. Elucidation of the biochemical pathway of 2-phenylethanol from shikimic acid using isolated protoplasts of rose flowers. Journal of Plant Physiology, 2009, 166(8): 887- 891.
[14] G. Berrah, W. A. Konetzka. Selective and reversible inhibition of the synthesis of bacterial deoxyribonucleic acid by phenethyl alcohol. Journal of Bacteriology, 1962, 83: 738.
[15] S. Silver, L. Wendt. Mechanism of action of phenethyl alcohol: Breakdown of the cellular permeability barrier. Journal of Bacteriology, 1967, 93: 560.
[16] M. Sasser. Inhibition by antibacterial compounds of the hypersensitive reaction induced by Pseudomonas pisi in tobacco. Phytopathology, 1982, 72: 1513-1517.
[17] S. Fraud, et al. Aromatic alcohols and their effect on Gram- negative bacteria, cocci and mycobacteria. Journal of Antim- icrobial Chemotherapy, 2003, 51(6): 1435-1436.
[18] E. K. Mo, C. K. Sung. Phenylethyl alcohol (PEA) application slows fungal growth and maintains aroma in strawberry. Post- harvest Biology and Technology, 2007, 45(2): 234-239.
[19] M. Sakai, et al. Production of 2-phenylethanol in roses as the dominant floral scent compound from L-phenylalanine by two key enzymes, a PLP-dependent decarboxylase and a phenylacetaldehyde reductase. Bioscience, Biotechnology, and Biochemis- try, 2007, 71(10): 2408-2419.
[20] D. Tieman, et al. Tomato aromatic amino acid decarboxylases participate in synthesis of the flavor volatiles 2-phenylethanol and 2-phenylacetaldehyde. Washington DC: National Academy of Sciences, 2006.
[21] 靖会, 佐建锋, 李教社. 苯乙醇苷类化合物的药理研究进展[J]. 时珍国医国药, 2006, 17(3): 440-441.
[22] 李刚, 朱文斌, 牛飞等. 肉苁蓉苯乙醇苷对大鼠精子体外氧化损伤的保护作用研究[J]. 时珍国医国药, 2010, 21(9): 2205- 2207.
[23] 刘兆荣, 刘宗歧. β-苯乙醇的合成方法与提纯[J]. 北京化工, 1993, 23(3): 33-38.
[24] 梅建凤. 利用酵母细胞生物转化法合成天然2-苯乙醇的研究[D]. 浙江大学, 2009.
[25] D. V. Banthorpe, et al. Accumulation of 2-phenylethanol by callus derived from leaf-bud of Rosa damascena. Phytochemistry, 1988, 27(3): 795-801.
[26] U. Krings, R. Berger. Biotechnological production of flavors and fragrances. Applied Microbiology and Biotechnology, 1998, 49(1): 1-8.
[27] J. Schrader. Microbial flavour production. Flavours and Fra- grances, 2007: 507-574.
[28] P. S. J. Cheetham. The use of biotransformations for the production of flavors and fragrances. Trends in Biotechnology, 1993, 11(11): 478-488.
[29] F. Ehrlich. Uber die bedingungen der fuselolbildung und uber ihren zusammenhang mit dem eiweißaufbau der Hefe. Berichte der Deutschen Chemischen Gesellschaft, 1907, 40(1): 1027- 1047.
[30] D. Vollbrecht, F. Radler. Formation of higher alcohols by amino acid deficient mutants of Saccharomyces cerevisiae. I. The decomposition of amino acids to higher alcohols. Archives of Mikrobiology, 1973, 94(4): 351-358.
[31] C. E. Fabre, J. S. Condoret and A. Marty. Extractive fermentation of aroma with supercritical CO2. Biotechnology and Bioengineering, 1999, 64(4): 392-400.
[32] D. Wilkie, N. Maroudas. Induction of cytoplasmic respiratory deficiency in yeast by phenethyl alcohol. Genetical Research, 1969, 13(1): 107-111.
[33] D. Stark, et al. Inhibition aspects of the bioconversion of-phenyl- alanine to 2-phenylethanol by Saccharomyces cerevisiae. Enzyme and Microbial Technology, 2003, 32(2): 212-223.
[34] E. Albertazzi, et al. Biogeneration of 2-phenylethanol and 2-phenyl- ethylacetate important aroma components. Biotechnology Letters, 1994, 16(5): 491-496.
[35] R. Seward, et al. The effects of ethanol, hexan-1-ol, and 2-phenylethanol on cider yeast growth, viability, and energy status; synergistic inhibition. Journal of the Institute of Brewing, 1996, 102: 439-444.
[36] D. Stark, et al. Extractive bioconversion of 2-phenylethanol from L-phenylalanine by Saccharomy cescerevisiae. Biotechnology Progress, 2002, 18(3): 514-523.
[37] D. Stark, et al. Novel type of in situ extraction: Use of solvent containing microcapsules for the bioconversion of 2-phenyl- ethanol from L-phenylalanine by Saccharomyces cerevisiae. Biotechnology and Bioengineering, 2003, 83(4): 376-385.
[38] A. Freeman, J. M. Woodley and M. D. Lilly. In situ product removal as a tool for bioprocessing. Nature Biotechnology, 1993, 11: 1007-1012.
[39] 崔志峰, 车智博, 杨霄等. 2-苯乙醇耐受性高产酵母菌株的选育[J]. 浙江工业大学学报, 2008, 36(4): 427-430.
[40] C. Fabre, et al. Extraction of 2-phenylethyl alcohol: By techniques such as adsorption, inclusion, supercritical CO2, liquid-liquid and membrane separations. Perfumer & Flavorist, 1996, 21: 27-40.
[41] 刘国, 陆军, 张伟国. 两相体系中菌体转化法制备2-苯乙醇的研究[J]. 生物技术, 2009, 19(3): 67-70.
[42] 梅建凤, 陈虹, 王鸿等. 水/有机溶剂两相体系中生物转化合成2-苯乙醇[J]. 化学反应工程与工艺, 2009, 25(1): 69-73.
[43] D. Stark, et al. Extractive bioconversion of 2-phenylethanol from L-phenylalanine by Saccharomyces cerevisiae. Biotechnology Progress, 2002, 18(3): 514-523.
[44] M. Etschmann, D. Sell and J. Schrader. Screening of yeasts for the production of the aroma compound 2-phenylethanol in a molasses-based medium. Bio-technology Letters, 2003, 25(7): 531-536.
[45] M. Etschmann. Medium optimization for the production of the aroma compound 2-phenylethanol using a genetic algorithm. Journal of Molecular Catalysis B: Enzymatic, 2004, 29(1-6): 187-193.
[46] M. M. Etschmann, J. Schrader. An aqueous-organic two-phase bioprocess for efficient production of the natural aroma chemicals 2-phenylethanol and 2-phenylethylacetate with yeast. Applied Microbiology and Biotechnology, 2006, 71(4): 440-443.
[47] F. Gao, A. J. Daugulis. Bioproduction of the aroma compound 2- phenylethanol in a solid-liquid two-phase partitioning bioreactor system by Kluyveromyces marxianus. Biotechnology and Bio- engineering, 2009, 104(2): 332-339.
[48] M. Sendovski, N. Nir and A. Fishman. Bioproduction of 2-phenylethanol in a biphasic ionic liquid aqueous system. Journal of Agricultural and Food Chemistry, 2010, 58(4): 2260- 2265.
[49] A. Klingenberg, H. Hanssen. Enhanced production of volatile flavour compounds from yeasts by adsorber techniques. I. Model investigations. Chemical and Biochemical Engineering, 1988, 2: 222-224.
[50] R. G. Berger. Aroma biotechnology. Berlin: Springer, 1995.
[51] 关昂, 王航, 孟春等. 原位转移技术用于酵母合成2-苯乙醇[J]. 过程工程学报, 2009, 9(1): 128-132.
[52] W. Bluemke. Enhanced production of natural aroma compounds through process-integrated pervaporation. Book of Abstracts: 3rd European Symposium on Biochemical Engineering Science, 2000: 285.
[53] S. Atsumi, T. Hanai and J. C. Liao. Non-fermentative pathways for synthesis of branched-chain higher alcohols as biofuels. Nature, 2008, 451: 86-89.
[54] L. P. Somogyi. The flavour and fragrance industry: Serving a global market. Chemical Industries, 1996: 170-173.
[55] K. Fukuda, et al. Breeding of brewing yeast producing a large amount of β-phenylethyl alcohol and β-phenylethyl acetate. Agricultural and Biological Chemistry, 1990, 54(1): 269-271.
[56] T. Luo, W. Fan and Y. Xu. Characterization of volatile and semi-volatile compounds in Chinese rice wines by headspace solid phase microextraction followed by gas chromatography-mass spectrometry. Journal of the Institute of Brewing, 2008, 114(2): 172-179.
[57] 陈双, 罗涛, 徐岩等. 我国黄酒酵母和酿酒原料对黄酒中β-苯乙醇含量的影响[J]. 中国酿造, 2009, 28(4): 23-26.
[58] 李丽, 刘春明, 刘志强等. 肉苁蓉中苯乙醇苷类化合物的分离提取及电喷雾质谱研究[J]. 质谱学报, 2006, 27(4): 232- 236.
[59] 张树军, 张军锋, 王金兰. 紫丁香树皮的化学成分研究[J]. 中草药, 2006, 37(11): 1624-1626.
[60] 王健, 李锦, 郭俊华等. HPLC测定退热颗粒中连翘酯苷含量[J]. 中国中药杂志, 2007, 32(9): 860.