日用化学工业 ›› 2019, Vol. 49 ›› Issue (7): 464-469.doi: 10.3969/j.issn.1001-1803.2019.07.008
收稿日期:
2018-09-19
修回日期:
2019-06-09
出版日期:
2019-07-25
发布日期:
2019-07-26
通讯作者:
崔励
作者简介:
王 迪(1992-),女,山东人,硕士研究生,电话:18742053265,E-mail: 基金资助:
Received:
2018-09-19
Revised:
2019-06-09
Online:
2019-07-25
Published:
2019-07-26
Contact:
Li CUI
摘要:
综述了生物法合成烷基糖苷,包括糖苷酶选择、酶促糖苷化、烷基糖苷的酶促合成等几个方面。与传统化学合成法相比,烷基糖苷的酶促合成提供了极好的环保升级替代方案,具有较大的利用潜能和广阔前景。未来烷基糖苷的酶促合成可以通过开发新型基因工程菌,采用全细胞催化的方法,进行工业化放大研究。
中图分类号:
王迪,吴令帆,崔励. 酶促合成烷基糖苷[J]. 日用化学工业, 2019, 49(7): 464-469.
WANG Di,WU Ling-fan,CUI Li. Enzymatic synthesis of alkyl glycosides[J]. China Surfactant Detergent & Cosmetics, 2019, 49(7): 464-469.
[1] | Wang Xuefeng, Zhang Jianjuan . Study on foam properties of APG suffactants[J]. Advanced Textile Technology, 2017,25(1) : 51-55. |
[2] | Liu Yang, Zhang Chunfeng, Wang Fengshou , et al. The latest research progress of alkyl polyglycosides[J]. Detergent and Cosmetics, 2016,39(4) : 25-29. |
[3] |
Salman S M, Heidelberg T ,ussen R S D, et al. Amide-based surfactants from methyl glucoside as potential emulsifiers[J]. Journal of Surfactants and Detergents, 2014,17(6) : 1141-1149.
doi: 10.1007/s11743-014-1628-8 |
[4] | Zhao J, Yang Q, Li X , et al. Enhanced production of short-chain fatty acid from food waste stimulated by alkyl polyglycosides and its mechanism[J]. Waste Management, 2015,46:133-139. |
[5] | Zhao J, Yang Q, Li X , et al. Effect of initial pH on short chain fatty acid production during the anaerobic fermentation of membrane bioreactor sludge enhanced by alkyl polyglcoside[J]. International Biodeterioration and Biodegradation, 2015,104:283-289. |
[6] | Bilanicova D, Mastihuba V, Mastihubova M , et al. Improvements in enzymatic preparation of alkyl glycosides[J]. Czech Journal of Food Sciences, 2010,28(1) : 69-73. |
[7] | Yang Rongling . Enzymatic synthesis of glycosides and their ester derivatives[D]. Guangzhou:South China University of Technology, 2010. |
[8] | Svensson D . Enzymatic synjournal of alkyl glycosides:new applications for glycoside hydrolases[J]. Biology and Life Sciences, 2009. |
[9] | Svensson D, Adlercreutz P . Immobilisation of CGTase for continuous production of long-carbohydrate-chain alkyl glycosides:Control of product distribution by flow rate adjustment[J]. Journal of Molecular Catalysis B:Enzymatic, 2011,69 : 147-153. |
[10] | Desmet T, Soetaert W, Bojarova P , et al. Enzymatic glycosylation of small molecules:challenging substrates require tailored catalysts[J]. Cheminform, 2012,18(35) : 10786-10801. |
[11] | Charoensapyanan R, Ito K, Rudeekulthamrong P , et al. Enzymatic synjournal of propyl-α-glycosides and their application as emulsifying and antibacterial agents[J]. Biotechnology and Bioprocess Engineering, 2016,21(3) : 389-401. |
[12] | Tang Yafang, Li Hu, Wang Cheng , et al. Synjournal of alkyl glycoside from canna edulis ker starch catalyzed by α-amylase[J]. Journal of Shanghai Jiaotong University (Agricultural Sciences) , 2014,32(6) : 38-43. |
[13] | Lan X, Liu J, Tang Y , et al. Structural identification of alkyl glycosides obtained from the conversion of canna starch by immobilized α-amylase from Aspergillus oryzae[J]. Starch-Stärke, 2016,69(3-4) : 1600036. |
[14] |
Bojarová P, Kren V . Glycosidases:a key to tailored carbohydrates[J] . Trends in Biotechnology, 2009,27(4) : 199-209.
doi: 10.1016/j.tibtech.2008.12.003 |
[15] | Gaudin T, Rotureau P, Pezron I , et al. Conformations of n-alkyl-α/β-d-glucopyranoside surfactants:Impact on molecular properties[J] . Computational and Theoretical Chemistry, 2017,1101:20-29. |
[16] | Chang Z, Lan H, Bao Y , et al. Progress of β-Glucosidase from Microorganisms[J]. Advances in Microbiology, 2018,7(2) : 79-86. |
[17] | Wei Binru, Liu Duanyu, Han Shuangyan , et al. Expression of aspergillus aculeatus β-GlycosidaseⅠgene in pichia pastoris and its application on the synthsis of alkyl glucoside[J]. Cemical Journal of Chinese Universtties, 2012,33(7) : 1498-1504. |
[18] | Guo Dongheng . Cell-surface display of β-glucosidase from Cassava in Pichia pastoris and the study on the synthesis of alkyl polyglycoside[D]. Guangdong:South China University of Technology, 2016. |
[19] | Mai Zhimao . Cloning expression and characterization of two β-glucosidase gene from marine microorganisms[D]. Beijing: University of Chinese Academy of Sciences, 2014. |
[20] | Yang Jingwen . Synthesis of glycoconjugates using thermostable glycosidases from Thermotoga naphthopila RUK-10[D]. Changchun:Jilin University, 2017. |
[21] |
James R, Cairns K, Esen A . β-Glucosidases[J]. Cellular and Molecular Life Sciences, 2010,67(20) : 3389-3405.
doi: 10.1007/s00018-010-0399-2 |
[22] | Zhou Linfang, Jiang Bo, Zhang Tao , et al. Research progress of β-glucosidases of glycoside hydrolase family 3[J]. Science and Technology of Food Industry, 2017,38(14) : 330-335. |
[23] | Yu Huilei, Xu Jianhe, Lin Guoqiang . Application of glycosidase to glycoside synjournal[J]. Chinese Journal of Organic Chemistry, 2006,26(8) : 1052-1058. |
[24] | Crout D H G, Vic G . Glycosidases and glycosyl transferases in glycoside and oligosaccharide synjournal[J]. Current Opinion in Chemical Biology, 1998,2(1) : 98-111. |
[25] | Balogh T, Boross L, Kosáry J . Novel reaction systems for the synjournal of β-glucosides by enzymatic reverse hydrolysis[J]. Tetrahedron, 2003,60(3) : 679-682. |
[26] | Moore B D, Partridge J, Halling P J. Very high activity biocatalysts for low-water systems[J].Humana Press, 2001: 97-104. |
[27] | Ljunger G, Adlercreutz P, Bo M . Enzymatic synjournal of octyl-β-glucoside in octanol at controlled water activity[J]. Enzyme and Microbial Technology, 1994,16(9) : 751-755. |
[28] | Li Hongwei . Research on the technics of APG’synthesie catalyzed by immobiled glucosidase in microcapsule[D]. Changchun:Jilin University, 2009. |
[29] | Wang Xiuzhen . Immobilized β-glucosidase and its application in the synthesis of alkyl glycosides[D]. Wuxi:Jiangnan University, 2009. |
[30] | Kawahara E, Fujii M, Kato K , et al. Chemoenzymatic synjournal of naturally occurring benzyl 6-O-glycosyl-β-D-glucopyranosides[J]. Chemical and Pharmaceutical Bulletin, 2005,53(8) : 1058. |
[31] | Akita H, Kawahara E, Kishida M , et al. Synjournal of naturally occurring β-D-glucopyranoside based on enzymatic β-glycosidation[J]. Journal of Molecular Catalusis B:Enzymatic, 2006,40(1) : 8-15. |
[32] | Basso A, Ducret A, Gardossi L , et al. Synjournal of octyl glucopyranoside by almond β-glucosidase adsorbed onto Celite R-649 ® [J]. Tetrahedron Letters, 2002,43(11) : 2005-2008. |
[33] |
Park D W, Kim H S, Jung J K , et al. Enzynatic synjournal of alkylylucosides by amphiphilia phase enzyme reaction[J]. Biotechnology Letters, 2000,22(11) : 951-956.
doi: 10.1023/A:1005620707624 |
[34] | Kumar P, Ryan B, Henehan G T M. β-Glucosidase from Streptomyces griseus:Nanoparticle immobilisation and alkyl glucoside synjournal[J]. Protein Expression and Purification, 2017,132:164-170. |
[35] | Yi Q, Sarney D B, Khan J A , et al. A novel approach to biotransformations in aqueous-organic two-phase systems:Enzymatic synjournal of alkyl β-[D]-glucosides using microencapsulated β-glucosidase[J]. Biotechnology and Bioengineering, 1998,60(3) : 385-390. |
[36] | Benesova E, Lipovova P, Dvorakova H . β-D-Galactosidase from Paenibacillus thiaminolyticus catalyzing transfucosylation reactions[J]. Glycobiology, 2009,20(4) : 442-451. |
[37] | Ito J, Ebe T, Shibasaki S , et al. Production of alkyl glucoside from cellooligosaccharides using yeast strains displaying Aspergillus aculeatus β-glucosidase[J]. Journal of Molecular Catalysis B:Enzymatic, 2007,49(1) : 92-97. |
[38] | Hronská H, Mastihuba V, Tokošová S , et al. Semicontinual synjournal of alkyl galactosides using β-galactosidase entrapped in polyvinylalcohol hydrogel[J]. Biocatalysis and Biotransformation, 2016,34(5) : 219-225. |
[39] | Sujittra S, Vichitphan K, Han J , et al. Hanseniaspora thailandica BC9 β-glucosidase for the production of β-D-hexyl glucoside[J]. Journal of Microbiology and Biotechnology, 2018,28(4) : 579-587. |
[40] | Rather M Y, Mishra S, Chand S . β-Glucosidase catalyzed synjournal of octyl-β-D-glucopyranoside using whole cells of Pichia etchellsii in micro aqueous media[J]. Journal of Biotechnology, 2010,150(4) : 490. |
[41] | Hu Xiayan, Liu Duanyu, Zheng Suiping . Optimization of the synjournal of alkyl glucoside catalyzed by aspergillus aculeatus β-glucosidase-displaying pichia pastoris whole-cells[J]. Biotechnology Bulletin, 2014 ( 6) : 205-210. |
[42] | Guo D, Xu Y, Kang Y , et al. Synjournal of octyl-β-D-glucopyranoside catalyzed by Thai rosewood β-glucosidase-displaying Pichia pastoris in an aqueous/organic two-phase system[J]. Enzyme and Microbial Technology, 2016,85:90-97. |
[43] | Svensson D, Ulvenlund S, Adlercreutz P . Enzymatic route to alkyl glycosides having oligomeric head groups[J]. Green Chemistry, 2009,11(8) : 1222-1226. |
[44] |
De Carvalho C C C R . Enzymatic and whole cell catalysis:Finding new strategies for old processes[J]. Biotechnology Advances, 2011,29(1) : 75-83.
doi: 10.1016/j.biotechadv.2010.09.001 |
[45] | Rather M Y, Mishra S, Verma V , et al. Biotransformation of methyl-β-D-glucopyranoside to higher chain alkyl glucosides by cell bound β-glucosidase of Pichia etchellsii[J]. Bioresource Technology, 2012,107:287. |
[46] |
Rather M Y, Mishra S, Aravinda S . Exploring the synthetic potential of cell bound β-glycosidase of Pichia etchellsii[J]. Journal of Biotechnology, 2013,165(1) : 63-68.
doi: 10.1016/j.jbiotec.2013.02.011 |
[1] | 艾浩康, 姜亚洁, 王亚魁, 张璐, 耿涛. 硬脂酸酯双子季铵盐的合成及性能研究[J]. 日用化学工业(中英文), 2024, 54(1): 16-23. |
[2] | 崔丛丛,张红丽,玄光善. 多头季铵盐表面活性剂的合成及性能评价[J]. 日用化学工业(中英文), 2023, 53(8): 899-907. |
[3] | 周媛, 杨秀全, 张军, 白亮, 吴志宇. 不同酯化度烷基糖苷磺基琥珀酸酯盐的合成与性能[J]. 日用化学工业(中英文), 2023, 53(7): 765-772. |
[4] | 李晓敏. 基于酶催化合成单甘油酯工艺优化及抑菌活性研究[J]. 日用化学工业(中英文), 2023, 53(2): 180-186. |
[5] | 王涛, 孙晓, 李卓, 董曼曼, 贾寒冰, 卫星华. 乙酰香兰素合成工艺优化及反应进程分析[J]. 日用化学工业(中英文), 2023, 53(11): 1273-1279. |
[6] | 米浩宇,刘婉怡,段虹钰,张天春,韩鲁平. 玉米秸秆木聚糖的硫酸化修饰及抗氧化活性研究[J]. 日用化学工业, 2022, 52(9): 975-980. |
[7] | 赵淑芬,郑丹苗,刘华溪,宋松林,陈站,杨泞源,韦星船. 松香基双子表面活性剂合成及应用进展[J]. 日用化学工业, 2022, 52(8): 892-903. |
[8] | 范婷,赵健烽,常烨珺,季乐. 重组人源化Ⅲ型胶原蛋白对皮肤功能性相关基因 表达的影响[J]. 日用化学工业(中英文), 2022, 52(12): 1326-1332. |
[9] | 范高宁. 类菌胞素氨基酸的性质及其在化妆品领域中应用的 研究进展[J]. 日用化学工业(中英文), 2022, 52(12): 1366-1372. |
[10] | 易瑞,徐春生. 密泡牙膏的试验研究[J]. 日用化学工业(中英文), 2022, 52(11): 1214-1220. |
[11] | 薛婉婷,李丽,董银卯,郭苗苗. 美白功效评价现状及发展趋势[J]. 日用化学工业, 2021, 51(9): 890-896. |
[12] | 任倩倩,吴华,金建明. 化妆品植物原料(IV)——抑制黑色素合成信号通路的植物美白原料的研究与开发[J]. 日用化学工业, 2021, 51(7): 590-597. |
[13] | 王军,张晨龙,杨许召,白亚榕. 磁性表面活性剂的研究进展[J]. 日用化学工业, 2021, 51(6): 546-553. |
[14] | 富多娇,周银,陈晗宇,刘红芹,徐宝财. 季铵盐型双子表面活性剂及其改性黏土的研究和应用进展[J]. 日用化学工业, 2021, 51(4): 338-347. |
[15] | 汪琴琴,李颜利,邹伟,颜杰,刘波,李慧. 短碳氟链缩合剂的绿色合成与应用[J]. 日用化学工业, 2021, 51(4): 288-293. |
|