Citation: YANG Le-Le, LIU Jia, LI Yue, LIU Kun, RUAN Wen-Juan. Molecular Recognition of Glycoconjugated Porphyrin with Chiral Amino Acid Methyl Ester[J]. Acta Physico-Chimica Sinica, ;2013, 29(09): 1877-1885. doi: 10.3866/PKU.WHXB201306143 shu

Molecular Recognition of Glycoconjugated Porphyrin with Chiral Amino Acid Methyl Ester

1.
Department of Chemistry, Nankai University, Tianjin 300071, P. R. China

Received Date: 19 April 2013
Available Online: 14 June 2013
Fund Project: 国家自然科学基金(20671053)资助项目 (20671053)

Three atropisomeric tetrasaccharide-substituted zinc porphyrins (αβαβ-Zn-A, ααββ-Zn-A and αααβ-Zn-A) and one monosaccharide-substituted zinc porphyrin (Zn-B) were synthesized. We explored the interactions of these zinc porphyrins with a set of amino acid methyl esters (L/D-LeuOMe, L/ D-ThrOMe, L/D-ValOMe, and L/D-PheOMe)using visible titration and circular dichroism (CD) spectroscopy. We observed that all of them bind to L-amino acid methyl esters more closely than to those with D-configuration. In particular, ααββ-Zn-A gives a high enantioselectivity, K_L/K_D of 4.75, and could be used for chiral recognition of amino acid methyl esters. The binding constants of the three Zn-A compounds with methyl amino acid methyl esters are in the same order, i.e., K^θ(LeuOMe) > K^θ(ValOMe) > K^θ(ThrOMe) > K^θ(PheOMe), but the order of the binding constants for K^θ(PheOMe) > K^θ(LeuOMe) > K^θ(ValOMe) > K^θ(ThrOMe). In addition, we used imidazole as a probe to study the effects of achiral molecules on the conformations of the glycoconjugated porphyrins. The experimental results show that binding with imidazole causes adjustments in the conformations of the Zn-A compounds. The binding constants of the Zn-A compounds with imidazole and with methyl amino acid methyl esters are in the same order: K^θ(ααββ-Zn-A) > K^θ(αβαβ-Zn-A) > K^θ(αααβ-Zn-A).
- Glycoconjugated porphyrin,
- Chiral recognition,
- Spectrum titration,
- Circular dichroism spectroscopy,
- Amino acid methyl ester
1. [1]
  
  (1) Berzin, B. D. Coordination Compounds of Porphyrins and Phthalocyanines;Wiley: NewYork, 1981; p 4.
2. [2]
  (2) Mizutani, T.; Ema, T.; Yoshida, T.; Kuroda, Y.; O shi, H.Inorg. Chem. 1993, 32 (10), 2072. doi: 10.1021/ic00062a032
3. [3]
  (3) Mizutani, T.; Ema, T.; Tomita, T.; Kuroda, Y.; O shi, H. J. Am. Chem. Soc. 1994, 116 (10), 4240. doi: 10.1021/ja00089a013
4. [4]
  (4) Collman, J. P.; Rapta, M.; Bröring, M.; Raptova, L.;Schwenninger, R.; Boitrel, B.; Fu, L.; L'Her, M. J. Am. Chem. Soc. 1999, 121 (6), 1387. doi: 10.1021/ja983351a
5. [5]
  (5) Liu, Y.; Li, B.; Wada, T.; Inoue, Y. Tetrahedron 2001, 57 (33),7153. doi: 10.1016/S0040-4020(01)00671-8
6. [6]
  (6) Mizuno, Y.; Aida, T.; Yamaguchi, K. J. Am. Chem. Soc. 2000,122 (22), 5278. doi: 10.1021/ja000052o
7. [7]
  (7) Collman, J. P.; Gagne, R. R.; Reed, C.; Halbert, T. R.; Lang, G.;Robinson, W. T. J. Am. Chem. Soc. 1975, 97 (6), 1427. doi: 10.1021/ja00839a026
8. [8]
  (8) Laville, I.; Pigaglio, S.; Blais, J.C.; Doz, F.; Loock, B.; Maillard,P.; Grierson, D. S.; Blais, J. J. Med. Chem. 2006, 49 (8), 2558.doi: 10.1021/ic00062a032
9. [9]
  (3) Mizutani, T.; Ema, T.; Tomita, T.; Kuroda, Y.; O shi, H. J. Am. Chem. Soc. 1994, 116 (10), 4240. doi: 10.1021/ja00089a013
10. [10]
  (4) Collman, J. P.; Rapta, M.; Bröring, M.; Raptova, L.;Schwenninger, R.; Boitrel, B.; Fu, L.; L'Her, M. J. Am. Chem. Soc. 1999, 121 (6), 1387. doi: 10.1021/ja983351a
11. [11]
  (5) Liu, Y.; Li, B.; Wada, T.; Inoue, Y. Tetrahedron 2001, 57 (33),7153. doi: 10.1016/S0040-4020(01)00671-8
12. [12]
  (6) Mizuno, Y.; Aida, T.; Yamaguchi, K. J. Am. Chem. Soc. 2000,122 (22), 5278. doi: 10.1021/ja000052o
13. [13]
  (7) Collman, J. P.; Gagne, R. R.; Reed, C.; Halbert, T. R.; Lang, G.;Robinson, W. T. J. Am. Chem. Soc. 1975, 97 (6), 1427. doi: 10.1021/ja00839a026
14. [14]
  (8) Laville, I.; Pigaglio, S.; Blais, J.C.; Doz, F.; Loock, B.; Maillard,P.; Grierson, D. S.; Blais, J. J. Med. Chem. 2006, 49 (8), 2558.
15. [15]
  (9) Wang, C. Z.; Zhu, Z. A.; Li, Y.; Chen, Y. T.; Wen, X.; Miao, F.M.; Chan, W. L.; Chan, A. S. C. New J. Chem. 2001, 25 (6),801. doi: 10.1039/b100942g
16. [16]
  (10) Maillard, P.; Guerquin-Kern, J. L.; Momenteau, M. Tetrahedron Lett. 1991, 32 (37), 4901. doi: 10.1016/S0040-4039(00)93491-9
17. [17]
  (11) Achelle, S.; Couleaud, P.; Baldeck, P.; Teulade-Fichou, M. P.;Maillard, P. Eur. J. Org. Chem. 2011, 2011 (7), 1271. doi: 10.1002/ejoc.v2011.7
18. [18]
  (12) Li, C.; Wong, W. T. Tetrahedron Lett. 2002, 43 (17), 3217. doi: 10.1016/S0040-4039(02)00497-5
19. [19]
  (13) Perrin, D. D.; Armare , W. L. F.; Perrin, D. R. Purification of Laboratory Chemicals, 2nd ed.; Industry Press: Beijing, 1987; p126; translated by Shi, Y. [Perrin, D. D.; Armare , W. L. F.;Perrin, D. R. 实验室化学药品的提纯方法,第二版.时雨,译.北京:化学工业出版社, 1987: 126.]doi: 10.1039/b100942g
20. [20]
  (10) Maillard, P.; Guerquin-Kern, J. L.; Momenteau, M. Tetrahedron Lett. 1991, 32 (37), 4901. doi: 10.1016/S0040-4039(00)93491-9
21. [21]
  (11) Achelle, S.; Couleaud, P.; Baldeck, P.; Teulade-Fichou, M. P.;Maillard, P. Eur. J. Org. Chem. 2011, 2011 (7), 1271. doi: 10.1002/ejoc.v2011.7
22. [22]
  (12) Li, C.; Wong, W. T. Tetrahedron Lett. 2002, 43 (17), 3217. doi: 10.1016/S0040-4039(02)00497-5
23. [23]
  (13) Perrin, D. D.; Armare , W. L. F.; Perrin, D. R. Purification of Laboratory Chemicals, 2nd ed.; Industry Press: Beijing, 1987; p126; translated by Shi, Y. [Perrin, D. D.; Armare , W. L. F.;Perrin, D. R. 实验室化学药品的提纯方法,第二版.时雨,译.北京:化学工业出版社, 1987: 126.]
24. [24]
  (14) Maillard, P.; Guerquin-Kern, J. L.; Huel, C.; Momenteau, M. J. Am. Chem. Soc. 1993, 58 (10), 2774.
25. [25]
  (15) Maillard, P.; Vilain, S.; Huel, C.; Momenteau, M. J. Am. Chem. Soc. 1994, 59 (10), 2887.
26. [26]
  (16) (a) Oulmi, D.; Maillard, P.; Guerquin-Kern, J. L.; Huel, C.;Momenteau, M. J. Am. Chem. Soc. 1995, 60 (6), 1554.
27. [27]
  (b) Zhang, X. H.; Jiao, Z.; Yan, W. W.; Ruan, W. J.; Zhu, Z. A.Acta Phys. -Chim. Sin. 2010, 26 (3), 701. [张晓红,矫志,闫伟伟,阮文娟, 朱志昂.物理化学学报, 2010, 26 (3), 701.]doi: 10.3866/PKU.WHXB20100306
28. [28]
  (17) Tomé, J. P. C.; Neves, M. G. P. M. S.; Tomé, A. C.; Cavaleiro, J.A. S.; Mendonca, A. F.; Pegado, I. N.; Duarte, R.; Valdeira, M.L. Bioorg. Med. Chem. 2005, 13 (12), 3878. doi: 10.1016/j.bmc.2005.04.015
29. [29]
  (18) Liang, Q. F.; Liu, J. J.; Chen, J. Tetrahedron Lett. 2011, 52 (31),3987. doi: 10.1016/j.tetlet.2011.05.081
30. [30]
  (19) Zhou, Y.; Zhao, M.; Wu, Y.; Li, C.; Wu, J.; Zheng, M.; Peng, L.;Peng, S. Bioorg. Med. Chem. 2010, 18 (6), 2165. doi: 10.1016/j.bmc.2010.01.075
31. [31]
  (20) Ruan, W. J.; Liu, T.; Zhu, Z. A. Acta. Chim. Sin. 2003, 61, 1000.[阮文娟,刘涛, 朱志昂.化学学报, 2003, 61, 1000.]doi: 10.3866/PKU.WHXB20100306
32. [32]
  (17) Tomé, J. P. C.; Neves, M. G. P. M. S.; Tomé, A. C.; Cavaleiro, J.A. S.; Mendonca, A. F.; Pegado, I. N.; Duarte, R.; Valdeira, M.L. Bioorg. Med. Chem. 2005, 13 (12), 3878. doi: 10.1016/j.bmc.2005.04.015
33. [33]
  (18) Liang, Q. F.; Liu, J. J.; Chen, J. Tetrahedron Lett. 2011, 52 (31),3987. doi: 10.1016/j.tetlet.2011.05.081
34. [34]
  (19) Zhou, Y.; Zhao, M.; Wu, Y.; Li, C.; Wu, J.; Zheng, M.; Peng, L.;Peng, S. Bioorg. Med. Chem. 2010, 18 (6), 2165. doi: 10.1016/j.bmc.2010.01.075
35. [35]
  (20) Ruan, W. J.; Liu, T.; Zhu, Z. A. Acta. Chim. Sin. 2003, 61, 1000.[阮文娟,刘涛, 朱志昂.化学学报, 2003, 61, 1000.]
36. [36]
  (21) (a) uterman, M. J. Am. Chem. Soc. 1959, 30 (5), 1139.
37. [37]
  (b) Nappa, M.; Valentine, J. S. J. Am. Chem. Soc. 1978, 100 (16), 5075.
38. [38]
  (22) Wang, S. J.; Zang, N.; Ruan, W. J.; Zhu, Z. A. Acta Phys. -Chim. Sin. 2008, 24 (3), 507. [王树军,臧娜,阮文娟, 朱志昂.物理化学学报, 2008, 24 (3), 507.] doi: 10.3866/PKU.WHXB20080328
39. [39]
  (23) O shi, H.; Mizutani, T. Accounts Chem. Res. 1998, 31 (2), 81.doi: 10.1021/ar9603165
40. [40]
  (24) Zhang, X. H.; Guo, H. R.; Jiao, Z.; Yan, W. W.; Ruan, W. J.;Zhu, Z. A. Acta Phys. -Chim. Sin. 2011, 27, 774. [张晓红, 郭洪瑞,矫志,闫伟伟, 阮文娟,朱志昂. 物理化学学报, 2011,27, 774.] doi: 10.3866/PKU.WHXB20110432
41. [41]
  (25) Wang, S. J.; Luo, D. B.; Ruan, W. J.; Zhu, Z. A.; Ma, Y. Acta Phys. -Chim. Sin. 2005, 21 (8), 834. [王树军, 罗代兵, 阮文娟,朱志昂,马毅.物理化学学报, 2005, 21 (8), 834.] doi: 10.3866/PKU.WHXB20050803
1. [1]
  Keying Qu , Jie Li , Ziqiu Lai , Kai Chen . Unveiling the Mystery of Chirality from Tartaric Acid. University Chemistry, 2024, 39(9): 369-378. doi: 10.12461/PKU.DXHX202310091
2. [2]
  Jin Tong , Shuyan Yu . Crystal Engineering for Supramolecular Chirality. University Chemistry, 2024, 39(3): 86-93. doi: 10.3866/PKU.DXHX202308113
3. [3]
  Tianlong Zhang , Rongling Zhang , Hongsheng Tang , Yan Li , Hua Li . Online Monitoring and Mechanistic Analysis of 3,5-diamino-1,2,4-triazole (DAT) Synthesis via Raman Spectroscopy: A Recommendation for a Comprehensive Instrumental Analysis Experiment. University Chemistry, 2024, 39(6): 303-311. doi: 10.3866/PKU.DXHX202312006
4. [4]
  Jizhou Liu , Chenbin Ai , Chenrui Hu , Bei Cheng , Jianjun Zhang . 六氯锡酸铵促进钙钛矿太阳能电池界面电子转移及其飞秒瞬态吸收光谱研究. Acta Physico-Chimica Sinica, 2024, 40(11): 2402006-. doi: 10.3866/PKU.WHXB202402006
5. [5]
  Renxiao Liang , Zhe Zhong , Zhangling Jin , Lijuan Shi , Yixia Jia . A Palladium/Chiral Phosphoric Acid Relay Catalysis for the One-Pot Three-Step Synthesis of Chiral Tetrahydroquinoline. University Chemistry, 2024, 39(5): 209-217. doi: 10.3866/PKU.DXHX202311024
6. [6]
  Tingyu Zhu , Hui Zhang , Wenwei Zhang . Exploration and Practice of Ideological and Political Education in the Course of Experiments on Chemical Functional Molecules: Synthesis and Catalytic Performance Study of Chiral Mn(III)Cl-Salen Complex. University Chemistry, 2024, 39(4): 75-80. doi: 10.3866/PKU.DXHX202311011
7. [7]
  Haiying Wang , Andrew C.-H. Sue . How to Visually Identify Homochiral Crystals. University Chemistry, 2024, 39(3): 78-85. doi: 10.3866/PKU.DXHX202309004
8. [8]
  Ping Song , Nan Zhang , Jie Wang , Rui Yan , Zhiqiang Wang , Yingxue Jin . Experimental Teaching Design on Synthesis and Antitumor Activity Study of Cu-Pyropheophorbide-a Methyl Ester. University Chemistry, 2024, 39(6): 278-286. doi: 10.3866/PKU.DXHX202310087
9. [9]
  Xilin Zhao , Xingyu Tu , Zongxuan Li , Rui Dong , Bo Jiang , Zhiwei Miao . Research Progress in Enantioselective Synthesis of Axial Chiral Compounds. University Chemistry, 2024, 39(11): 158-173. doi: 10.12461/PKU.DXHX202403106
10. [10]
  Lirui Shen , Kun Liu , Ying Yang , Dongwan Li , Wengui Chang . Synthesis and Application of Decanedioic Acid-N-Hydroxysuccinimide Ester: Exploration of Teaching Reform in Comprehensive Applied Chemistry Experiment. University Chemistry, 2024, 39(8): 212-220. doi: 10.3866/PKU.DXHX202312035
11. [11]
  Zhuomin Zhang , Hanbing Huang , Liangqiu Lin , Jingsong Liu , Gongke Li . Course Construction of Instrumental Analysis Experiment: Surface-Enhanced Raman Spectroscopy for Rapid Detection of Edible Pigments. University Chemistry, 2024, 39(2): 133-139. doi: 10.3866/PKU.DXHX202308034
12. [12]
  Jingyi Chen , Fu Liu , Tiejun Zhu , Kui Cheng . Practice of Integrating Ideological and Political Education into Raman Spectroscopy Analysis Experiment Course. University Chemistry, 2024, 39(2): 140-146. doi: 10.3866/PKU.DXHX202310111
13. [13]
  Chun-Lin Sun , Yaole Jiang , Yu Chen , Rongjing Guo , Yongwen Shen , Xinping Hui , Baoxin Zhang , Xiaobo Pan . Construction, Performance Testing, and Practical Applications of a Home-Made Open Fluorescence Spectrometer. University Chemistry, 2024, 39(5): 287-295. doi: 10.3866/PKU.DXHX202311096
14. [14]
  Tianlong Zhang , Jiajun Zhou , Hongsheng Tang , Xiaohui Ning , Yan Li , Hua Li . Virtual Simulation Experiment for Laser-Induced Breakdown Spectroscopy (LIBS) Analysis. University Chemistry, 2024, 39(6): 295-302. doi: 10.3866/PKU.DXHX202312049
15. [15]
  Wei Peng , Baoying Wen , Huamin Li , Yiru Wang , Jianfeng Li . Exploration and Practice on Raman Scattering Spectroscopy Experimental Teaching. University Chemistry, 2024, 39(8): 230-240. doi: 10.3866/PKU.DXHX202312062
16. [16]
  Zhaoyue Lü , Zhehao Chen , Yi Ni , Duanbin Luo , Xianfeng Hong . Multi-Level Teaching Design and Practice Exploration of Raman Spectroscopy Experiment. University Chemistry, 2024, 39(11): 304-312. doi: 10.12461/PKU.DXHX202402047
17. [17]
  Conghao Shi , Ranran Wang , Juli Jiang , Leyong Wang . The Illustration on Stereoisomers of Macrocycles Containing Multiple Chiral Centers via Tröger Base-based Macrocycles. University Chemistry, 2024, 39(7): 394-397. doi: 10.3866/PKU.DXHX202311034
18. [18]
  Mengyao Shi , Kangle Su , Qingming Lu , Bin Zhang , Xiaowen Xu . Determination of Potassium Content in Tobacco Stem Ash by Flame Atomic Absorption Spectroscopy. University Chemistry, 2024, 39(10): 255-260. doi: 10.12461/PKU.DXHX202404105
19. [19]
  Yan Li , Xinze Wang , Xue Yao , Shouyun Yu . Kinetic Resolution Enabled by Photoexcited Chiral Copper Complex-Mediated Alkene E→Z Isomerization: A Comprehensive Chemistry Experiment for Undergraduate Students. University Chemistry, 2024, 39(5): 1-10. doi: 10.3866/PKU.DXHX202309053
20. [20]
  Min WANG , Dehua XIN , Yaning SHI , Wenyao ZHU , Yuanqun ZHANG , Wei ZHANG . Construction and full-spectrum catalytic performance of multilevel Ag/Bi/nitrogen vacancy g-C₃N₄/Ti₃C₂T_x Schottky junction. Chinese Journal of Inorganic Chemistry, 2024, 40(6): 1123-1134. doi: 10.11862/CJIC.20230477

Get Citation

PDF

XML

Metrics

PDF Downloads(598)
Abstract views(701)
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