Citation: LIU Ying, MENG Xiang-Guang, YU Wei-Feng, LI Xiao-Hong, PENG Xiao. Hydrolysis of Methyl-β-D-cellobioside Catalyzed by Functional Micelles with Glutamic Acid under Mild Conditions[J]. Acta Physico-Chimica Sinica, ;2013, 29(10): 2263-2270. doi: 10.3866/PKU.WHXB201307292 shu

Hydrolysis of Methyl-β-D-cellobioside Catalyzed by Functional Micelles with Glutamic Acid under Mild Conditions

1.
Key Laboratory of Green Chemistry and Technology, Ministry of Education, College of Chemistry, Sichuan University, Chengdu 610064, P. R. China

Received Date: 13 May 2013
Available Online: 29 July 2013
Fund Project: 国家自然科学基金(21073126, 21273156)资助项目 (21073126, 21273156)

Asurfactant with long alkyl chains and glutamic acid, N^α-dodecyl-L-glutamic acid, was synthesized. Micelles of this surfactant were used to catalyze the hydrolysis of methyl-β-D-cellobioside (MCB), a model substrate of cellulose, under mild conditions. The results indicate that the functional micelle displayed effective catalytic activity for the hydrolysis of MCB to glucose at low temperature (90℃) and an optimal pH of 5.0. The first-order reaction rate constant (k_m) of MCB hydrolysis catalyzed by the synthesized micelles was calculated based on the phase separation model of micellar catalysis. The hydrolysis of MCB catalyzed by the cooperative systems of micelles with glutamic acid (Glu) or histidine (His) was also investigated. The addition of amino acids promoted the hydrolysis of MCB, and the maximumcatalytic efficiency was reached at a molar concentration ratio of micelles to amino acids of 1:1. Temperature considerably influenced the reaction rate and product of MCB hydrolysis. The yield of glucose from MCB hydrolysis catalyzed by the cooperative system of micelles with Glu reached more than 36.6%after 1.5 h at 130℃. The kinetics of this reaction was studied; the apparent first-order rate constants (k_obsd) were obtained and the activation energy (E_a) calculated for the formation of glucose was 97.18 kJ·mol^-1.
- Methyl-β-D-cellobioside,
- Glutamic acid,
- Histidine,
- Micelle,
- Cellulose,
- Catalytic hydrolysis
1. [1]
  
  (1) Dhepe, P. L.; Fukuoka, A. ChemSusChem 2008, 1 (12), 969.doi: 10.1002/cssc.v1:12
2. [2]
  (2) Bozell, J. J.; Petersen, G. R. Green Chem. 2010, 12 (4), 539.doi: 10.1039/b922014c
3. [3]
  (3) Igarashi, K.; Uchihashi, T.; Koivula, A.; Wada, M.; Kimura, S.;Okamoto, T.; Penttilä, M.; Ando, T.; Samejima, M. Science2011, 333 (6047), 1279. doi: 10.1126/science.1208386
4. [4]
  (4) Lynd, L. R.; Laser, M. S.; Bransby, D.; Dale, B. E.; Davison, B.;Hamilton, R.; Himmel, M.; Keller, M.; McMillan, J. D.;Sheehan, J.;Wyman, C. E. Nat. Biotechnol. 2008, 26 (2), 169.doi: 10.1038/nbt0208-169
5. [5]
  (5) Wolfenden, R.; Yuan, Y. J. Am. Chem. Soc. 2008, 130 (24),7548. doi: 10.1021/ja802206s
6. [6]
  (6) Komanoya, T.; Kobayashi, H.; Hara, K.; Chun, W. J.; Fukuoka,A. Appl. Catal. A-Gen. 2011, 407 (1-2), 188.
7. [7]
  (7) Harmer, M. A.; Fan, A.; Liauw, A.; Kumar, R. K. Chem. Commun. 2009, No. 43, 6610.
8. [8]
  (8) Nie, H. R.; Liu, M. Z.; Chen, Z. B. Acta Phys. -Chim. Sin. 2004,20 (4), 386. [聂华荣,柳明珠,陈振斌.物理化学学报, 2004,20 (4), 386.] doi: 10.3866/PKU.WHXB20040411
9. [9]
  (9) Wilson, D. B. Curr. Opin. Biotech. 2009, 20 (3), 295. doi: 10.1016/j.copbio.2009.05.007
10. [10]
  (10) Rinaldi, R.; Palkovits, R.; Schuth, F. Angew. Chem. Int. Edit.2008, 47 (42), 8047. doi: 10.1002/anie.v47:42
11. [11]
  (11) Kitano, M.; Yamaguchi, D.; Suganuma, S.; Nakajima, K.; Kato,H.; Hayashi, S.; Hara, M. Langmuir 2009, 25 (9), 5068. doi: 10.1021/la8040506
12. [12]
  (12) Wang, H. Y.; Zhang, C. B.; He, H.; Wang, L. Acta Phys. -Chim. Sin. 2010, 26 (7), 1873. [王华瑜, 张长斌,贺泓,王莲.物理化学学报, 2010, 26 (7), 1873.] doi: 10.3866/PKU.WHXB20100721
13. [13]
  (13) Long, J. X.; Guo, B.; Li, X. H.; Wang, F. R.; Wang, L. F. Acta Phys. -Chim. Sin. 2011, 27 (5), 995. [龙金星,郭斌,李雪辉,王芙蓉, 王乐夫.物理化学学报, 2011, 27 (5), 995.] doi: 10.3866/PKU.WHXB20110506
14. [14]
  (14) Singhania, R. R.; Patel, A. K.; Sukumaran, R. K.; Larroche, C.;Pandey, A. Bioresource Technol. 2013, 127, 500. doi: 10.1016/j.biortech.2012.09.012
15. [15]
  (15) Koshland, D. E. J.; Stein, S. S. J. Biol. Chem. 1954, 208 (1), 139.
16. [16]
  (16) Wang, J. H.; Hou, Q. Q.; Dong, L. H.; Liu, Y. J.; Liu, C. B.J. Mol. Graph. Model. 2011, 30, 148. doi: 10.1016/j.jmgm.2011.06.012
17. [17]
  (17) Verma, M. L.; Chaudhary, R.; Tsuzuki, T.; Barrow, C. J.; Puri,M. Bioresource Technol. 2013, 135, 2. doi: 10.1016/j.biortech.2013.01.047
18. [18]
  (18) Figueira, J. A.; Sato, H. H.; Fernandes, P. J. Agric. Food Chem.2013, 61 (3), 626. doi: 10.1021/jf304594s
19. [19]
  (19) Muñoz-Gutiérrez, I.; Oropeza, R.; sset, G.; Martinez, A.J. Ind. Microbiol. Biot. 2012, 39 (8), 1141.
20. [20]
  (20) Liu, L. F.; Zeng, Z. T.; Zeng, G. M.; Chen, M.; Zhang, Y.;Zhang, J. C.; Fang, X.; Jiang, M.; Lu, L. H. Bioorg. Med. Chem. Lett. 2012, 22 (2), 837. doi: 10.1016/j.bmcl.2011.12.053
21. [21]
  (21) Jiang, F. B.; Jiang, B. Y.; Cao, Y. S.; Meng, X. G.; Yu, X. Q.;Zeng, X. C. Colloids Surf. A 2005, 254 (1-3), 91.
22. [22]
  (22) Bhattacharya, S.; Kumari, N. Coord. Chem. Rev. 2009, 253 (17-18), 2133. doi: 10.1016/j.ccr.2009.01.016
23. [23]
  (23) Desbouis, D.; Troitsky, I. P.; Belousoff, M. J.; Spiccia, L.;Graham, B. Coord. Chem. Rev. 2012, 256 (11-12), 897.
24. [24]
  (24) Boudou, M.; Ogawa, C.; Kobayashi, S. Adv. Synth. Catal. 2006,348 (18), 2585.
25. [25]
  (25) Ye, Y.; Ding, Q. P.;Wu, J. Tetrahedron 2008, 64 (7), 1378. doi: 10.1016/j.tet.2007.11.055
26. [26]
  (26) Mo, Z. L.; Sun, Y. X.; Chen, H.; Wang, K. J.; Liu, Y. Z.; Li, H. J.Acta Chim. Sin. 2005, 63 (14), 1365. [莫尊理, 孙银霞,陈红, 王坤杰, 刘艳芝, 李贺军. 化学学报, 2005, 63 (14),1365.]
27. [27]
  (27) Sasidharan, M.; Gunawardhana, N.; Luitel, H. N.; Yokoi, T.;Inoue, M.; Yusa, S.; Watari, T.; Yoshio, M.; Tatsumi, T.;Nakashima, K. J. Colloid Interface Sci. 2012, 370 (1), 51. doi: 10.1016/j.jcis.2011.12.050
28. [28]
  (28) Jiang, F. B.; Huang, L. Y.; Meng, X. G.; Du, J.; Yu, X. Q.; Zhao,Y. F.; Zeng, X. C. J. Colloid Interface Sci. 2006, 303 (1),236. doi: 10.1016/j.jcis.2006.07.050
29. [29]
  (29) Kou, D.; Meng, X. G.; Liu, Y.; Du, J.; Kou, X. M.; Zeng, X. C.Colloids Surf. A 2008, 324 (1-3), 189.
30. [30]
  (30) Li, J. H.; Du, L. K.; Wang, L. S. J. Phys. Chem. B 2010, 114 (46), 15261. doi: 10.1021/jp1064177
31. [31]
  (31) Barr, B. K.; Wolfgang, D. E.; Piens, K.; Claeyssens, M.; Wilson,D. B. Biochemistry 1998, 37 (26), 9220. doi: 10.1021/bi980063i
32. [32]
  (32) Zechel, D. L.; Withers, S. G. Accounts Chem. Res. 2000, 33 (1),11. doi: 10.1021/ar970172
33. [33]
  (33) Meiland, M.; Heinze, T.; Guenther, W.; Liebert, T. Carbohyd. Res. 2010, 345 (2), 257. doi: 10.1016/j.carres.2009.11.007
34. [34]
  (34) Cheng, M. X.; Shi, T.; Guan, H. Y.; Wang, S. T.; Wang, X. H.;Jiang, Z. J. Appl. Catal. B: Environ. 2011, 107 (1-2), 104.
35. [35]
  (35) Zhang, Y.; Xu, J. L.; Qi, W.; Yuan, Z. H.; Zhuang, X. S.; Liu, Y.;He, M. C. Appl. Biochem. Biotechnol. 2012, 168 (1), 144. doi: 10.1007/s12010-011-9362-4
36. [36]
  (36) Saqib, A. A. N.; Whitney, P. J. Biomass Bioenerg. 2011, 35 (11),4748. doi: 10.1016/j.biombioe.2011.09.013
37. [37]
  (37) Ruiz, M. D. C. R.; Querner, J.; Adorjan, I.; Kosma, P.; Rosenau,T. Macromol. Symp. 2005, 232 (1), 68.
38. [38]
  (38) Petersen, S. H.; Vanzyl, W. H.; Pretorius, I. S. Biotechnol. Tech.1998, 12 (8), 615. doi: 10.1023/A:1008829129516
39. [39]
  (39) Violot, S.; Aghajari, N.; Czjzek, M.; Feller, G.; Sonan, G. K.; uet, P.; Gerday, C.; Haser, R.; Receveur-Bréchot, V. J. Mol. Biol. 2005, 348 (5), 1211. doi: 10.1016/j.jmb.2005.03.026
40. [40]
  (40) Liu, J. L.; Wang, X. M.; Xu. D. G. J. Phys. Chem. B 2010, 114 (3), 1462. doi: 10.1021/jp909177e
41. [41]
  (41) Meng, X. G.; Guo, Y.; Hu, C. W.; Zeng, X. C. J. Inorg. Biochem. 2004, 98 (12), 2107. doi: 10.1016/j.jinorgbio.2004.09.019
42. [42]
  (42) Dwars, T.; Paetzold, E.; Oehme, G. Angew. Chem. Int. Edit.2005, 44 (44), 7174.
43. [43]
  (43) Menger, F. M.; Portnoy, C. E. J. Am. Chem. Soc. 1967, 89 (18),4698. doi: 10.1021/ja00994a023
44. [44]
  (44) Zeng, X. C.; Meng, X. G.; Wang, Q.; Zhang, Y. Q.; Qin, Z. M.J. Disper. Sci. Technol. 1997, 18 (4), 369. doi: 10.1080/01932699708943741
45. [45]
  (45) Zeng, X. C.; Wang, Q.; Meng, X. G.; Zhang, Y. Q.; Qin, Z. M.J. Disper. Sci. Technol. 1998, 19 (5), 591. doi: 10.1080/01932699808913201
46. [46]
  (46) Knowles, J. K. C.; Lentovaara, P.; Murray, M.; Sinnott, M. L.J. Chem. Soc., Chem. Commun. 1988, No. 21, 1401. doi: 10.1039/C39880001401
47. [47]
  (47) Claeyssens, M.; Tomme, P.; Brewer, C. F.; Hehre, E. J. FEBS Lett. 1990, 263 (1), 89.
48. [48]
  (48) Barr, B. K.; Wolfgang, D. E.; Piens, K.; Claeyssens, M.; Wilson,D. B. Biochemistry 1998, 37 (26), 9220. doi: 10.1021/bi980063i
49. [49]
  (49) Zechel, D. L.; Withers, S. G. Accounts Chem. Res. 2000, 33 (1),11. doi: 10.1021/ar970172+
50. [50]
  (50) Matson, T. D.; Barta, K.; Iretskii, A. V.; Ford, P. C. J. Am. Chem. Soc. 2011, 133 (35), 14090. doi: 10.1021/ja205436c
51. [51]
  (51) Potvin, J.; Sorlien, E.; Hegner, J.; DeBoef, B.; Lucht, B. L.Tetrahedron Lett. 2011, 52 (44), 5891.
52. [52]
  (52) Liang, X.; Montoya, A.; Haynes, B. S. J. Phys. Chem. B 2011,115 (36), 10682. doi: 10.1021/jp204199h
53. [53]
  (53) Sasaki, M.; Adschiri, T.; Arai, K. AIChE J. 2004, 50 (1), 192.
1. [1]
  Fanpeng Shang , Jiantuo Chen . 多视角分析DMPE盘状双层胶束——第38届中国化学奥林匹克(初赛)第4题解析. University Chemistry, 2025, 40(8): 388-393. doi: 10.12461/PKU.DXHX202410034
2. [2]
  Xiaoning TANG , Junnan LIU , Xingfu YANG , Jie LEI , Qiuyang LUO , Shu XIA , An XUE . Effect of sodium alginate-sodium carboxymethylcellulose gel layer on the stability of Zn anodes. Chinese Journal of Inorganic Chemistry, 2024, 40(8): 1452-1460. doi: 10.11862/CJIC.20240191
3. [3]
  Yan'e LIU , Shengli JIA , Yifan JIANG , Qinghua ZHAO , Yi LI , Xinshu CHANG . MoO₃/cellulose derived carbon aerogel: Fabrication and performance as cathode for lithium-sulfur battery. Chinese Journal of Inorganic Chemistry, 2025, 41(8): 1565-1573. doi: 10.11862/CJIC.20250054
4. [4]
  Lisha LEI , Wei YONG , Yiting CHENG , Yibo WANG , Wenchao HUANG , Junhuan ZHAO , Zhongjie ZHAI , Yangbin DING . Application of regenerated cellulose and reduced graphene oxide film in synergistic power generation from moisture electricity generation and Mg-air batteries. Chinese Journal of Inorganic Chemistry, 2025, 41(6): 1151-1161. doi: 10.11862/CJIC.20240202
5. [5]
  Feiyang Liu , Liuhong Song , Miaoyu Fu , Zhi Zheng , Gang Xie , Junlong Zhao . Tryptophan’s Employment Journey. University Chemistry, 2024, 39(9): 16-21. doi: 10.12461/PKU.DXHX202404037
6. [6]
  Hong Lu , Yidie Zhai , Xingxing Cheng , Yujia Gao , Qing Wei , Hao Wei . Advancements and Expansions in the Proline-Catalyzed Asymmetric Aldol Reaction. University Chemistry, 2024, 39(5): 154-162. doi: 10.3866/PKU.DXHX202310074
7. [7]
  Shijie Li , Ke Rong , Xiaoqin Wang , Chuqi Shen , Fang Yang , Qinghong Zhang . Design of Carbon Quantum Dots/CdS/Ta₃N₅ S-scheme Heterojunction Nanofibers for Efficient Photocatalytic Antibiotic Removal. Acta Physico-Chimica Sinica, 2024, 40(12): 2403005-0. doi: 10.3866/PKU.WHXB202403005
8. [8]
  Juan WANG , Zhongqiu WANG , Qin SHANG , Guohong WANG , Jinmao LI . NiS and Pt as dual co-catalysts for the enhanced photocatalytic H₂ production activity of BaTiO₃ nanofibers. Chinese Journal of Inorganic Chemistry, 2024, 40(9): 1719-1730. doi: 10.11862/CJIC.20240102
9. [9]
  Meiyu Lin , Yuxin Fang , Songzhang Shen , Yaqian Duan , Wenyi Liang , Chi Zhang , Juan Su . Exploration and Implementation of a Dual-Pathway Blended Teaching Model in General Chemistry Experiment Course: A Case Study of Copper Glycine Synthesis and Its Thermal Analysis. University Chemistry, 2024, 39(8): 48-53. doi: 10.3866/PKU.DXHX202312042
10. [10]
  Mengyang LI , Hao XU , Zhonghao NIU , Chunhua GONG , Weihui ZHONG , Jingli XIE . Highly effective catalytic synthesis of β-amino alcohols by using viologen-polyoxometalate hybrid materials. Chinese Journal of Inorganic Chemistry, 2025, 41(7): 1294-1300. doi: 10.11862/CJIC.20250080
11. [11]
  Meiran Li , Yingjie Song , Xin Wan , Yang Li , Yiqi Luo , Yeheng He , Bowen Xia , Hua Zhou , Mingfei Shao . Nickel-Vanadium Layered Double Hydroxides for Efficient and Scalable Electrooxidation of 5-Hydroxymethylfurfural Coupled with Hydrogen Generation. Acta Physico-Chimica Sinica, 2024, 40(9): 2306007-0. doi: 10.3866/PKU.WHXB202306007
12. [12]
  Yiping HUANG , Liqin TANG , Yufan JI , Cheng CHEN , Shuangtao LI , Jingjing HUANG , Xuechao GAO , Xuehong GU . Hollow fiber NaA zeolite membrane for deep dehydration of ethanol solvent by vapor permeation. Chinese Journal of Inorganic Chemistry, 2025, 41(2): 225-234. doi: 10.11862/CJIC.20240224
13. [13]
  Xiaoyang Li , Xiaowei Huang , Yimeng Zhang , Huan Liu , Shao Jin , Junpeng Zhuang . Comprehensive Chemical Experiments on the Synthesis of 1,3-Dibromo-5,5-Dimethylhydantoin and Its Application as a Brominating Reagent. University Chemistry, 2025, 40(7): 286-293. doi: 10.12461/PKU.DXHX202408035
14. [14]
  Yichang Liu , Li An , Dan Qu , Zaicheng Sun . “双碳”背景下的综合设计实验——以PbCrO₄催化甲基蓝的光降解速率常数测定为例. University Chemistry, 2025, 40(6): 222-229. doi: 10.12461/PKU.DXHX202407105
15. [15]
  Xiaojing Tian , Zhichun Huang , Qingsong Zhang , Xu Wang , Ning Yang , Nanping Deng . PNIPAm Thermo-Responsive Nanofibers Mats: Morphological Stability and Response Behavior under Cross-Linking. Acta Physico-Chimica Sinica, 2024, 40(4): 2304037-0. doi: 10.3866/PKU.WHXB202304037
16. [16]
  Yukun Xing , Xiaoyu Xie , Fangfang Chen . A Sunlit Gift: Vitamin D. University Chemistry, 2024, 39(9): 28-34. doi: 10.12461/PKU.DXHX202402006
17. [17]
  Aiyi Xin , Jiawei Li , Xinyang Ran , Chuanjiang Fu , Zhiguo Wang . Collaborative Science and Education Based Experimental Design in Organic Chemistry: A Case Study of the Nucleophilic Substitution Reaction of 2-Hydroxymethyl-4,6-Di-Tert-Butylphenol. University Chemistry, 2025, 40(5): 366-375. doi: 10.12461/PKU.DXHX202407031
18. [18]
  Jun Huang , Pengfei Nie , Yongchao Lu , Jiayang Li , Yiwen Wang , Jianyun Liu . 丝光沸石负载自支撑氮掺杂多孔碳纳米纤维电容器及高效选择性去除硬度离子. Acta Physico-Chimica Sinica, 2025, 41(7): 100066-0. doi: 10.1016/j.actphy.2025.100066
19. [19]
  Ying Li , Yushen Zhao , Kai Chen , Xu Liu , Tingfeng Yi , Li-Feng Chen . Rational Design of Cross-Linked N-Doped C-Sn Nanofibers as Free-Standing Electrodes towards High-Performance Li-Ion Battery Anodes. Acta Physico-Chimica Sinica, 2024, 40(3): 2305007-0. doi: 10.3866/PKU.WHXB202305007
20. [20]
  Yukun Chang , Haoqin Huang , Baolei Wang . Preparation of Trans-Cinnamic Acid via “One-Pot” Protocol of Aldol Condensation-Hydrolysis Reaction: Recommending an Improved Organic Synthesis Experiment. University Chemistry, 2024, 39(4): 322-328. doi: 10.3866/PKU.DXHX202309095

Get Citation

PDF

XML

Metrics

PDF Downloads(623)
Abstract views(872)
HTML views(10)

通讯作者: 陈斌, bchen63@163.com

1.
沈阳化工大学材料科学与工程学院沈阳 110142