Carbohydrate recognition by porphyrin-based molecularly imprinted polymers

Organic Letters

Volumn 7, Issue 6, 2005, Pages 963-966

  Lee, Jung Deog ^a   Greene, Nathaniel T ^b   Rushton, Gregory T ^c   Shimizu, Ken D ^b   Hong, Jong In ^a,d  

^a Seoul National University   (South Korea)

^b UNIVERSITY OF SOUTH CAROLINA   (United States)

^c KENNESAW STATE UNIVERSITY   (United States)

^d Korea Advanced Institute of Science and Technology (KAIST)   (South Korea)

Author keywords

[No Author keywords available]

Indexed keywords

CARBOHYDRATE; MONOMER; POLYMER; PORPHYRIN; UREA;

ARTICLE; BAY REGION BINDING SITE; CARBOHYDRATE ANALYSIS; CHEMICAL STRUCTURE; MOLECULAR IMPRINTING; MOLECULAR MIMICRY; MOLECULAR RECOGNITION; POLYMER PRODUCTION; RECEPTOR AFFINITY; STRUCTURE ANALYSIS;

BINDING SITES; CARBOHYDRATES; MOLECULAR STRUCTURE; POLYMERS; PORPHYRINS; UREA;

EID: 18244369452     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol047618o     Document Type: Article

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23. Studies on imprinting of sugar: (a) Mayes, A. G.; Andersson, L. I.; Mosbach, K. Anal. Biochem. 1994, 222, 483-488. (b) Wulff, G.; Schauhoff, S. J. Org. Chem. 1991, 56, 395-400. (c) Wang, W.; Gao, S.; Wang, B. Org. Lett. 1999, 1, 1209-1212. (d) Striegler, S. Tetrahedron 2001, 57, 2349-2354. (e) Striegler, S. Macromolecules 2003, 36, 1310-1317. (f) Ishi-i, T.; Iguchi, R.; Shinkai, S. Tetrahedron 1999, 55, 3883-3892. (g) Friggeri, A.; Kobayashi, H.; Shinkai, S.; Reinhoudt, D. N. Angew. Chem., Int. Ed. 2001, 40, 4729-4731. (h) Malitesta, C.; Losito, I.; Zambonin, P. G. Anal. Chem. 1999, 71, 1366-1370. (i) Parmpi, P.; Kofinas, P. Biomaterials 2004, 25, 1969-1973.
24. Studies on imprinting of sugar: (a) Mayes, A. G.; Andersson, L. I.; Mosbach, K. Anal. Biochem. 1994, 222, 483-488. (b) Wulff, G.; Schauhoff, S. J. Org. Chem. 1991, 56, 395-400. (c) Wang, W.; Gao, S.; Wang, B. Org. Lett. 1999, 1, 1209-1212. (d) Striegler, S. Tetrahedron 2001, 57, 2349-2354. (e) Striegler, S. Macromolecules 2003, 36, 1310-1317. (f) Ishi-i, T.; Iguchi, R.; Shinkai, S. Tetrahedron 1999, 55, 3883-3892. (g) Friggeri, A.; Kobayashi, H.; Shinkai, S.; Reinhoudt, D. N. Angew. Chem., Int. Ed. 2001, 40, 4729-4731. (h) Malitesta, C.; Losito, I.; Zambonin, P. G. Anal. Chem. 1999, 71, 1366-1370. (i) Parmpi, P.; Kofinas, P. Biomaterials 2004, 25, 1969-1973.
25. Studies on imprinting of sugar: (a) Mayes, A. G.; Andersson, L. I.; Mosbach, K. Anal. Biochem. 1994, 222, 483-488. (b) Wulff, G.; Schauhoff, S. J. Org. Chem. 1991, 56, 395-400. (c) Wang, W.; Gao, S.; Wang, B. Org. Lett. 1999, 1, 1209-1212. (d) Striegler, S. Tetrahedron 2001, 57, 2349-2354. (e) Striegler, S. Macromolecules 2003, 36, 1310-1317. (f) Ishi-i, T.; Iguchi, R.; Shinkai, S. Tetrahedron 1999, 55, 3883-3892. (g) Friggeri, A.; Kobayashi, H.; Shinkai, S.; Reinhoudt, D. N. Angew. Chem., Int. Ed. 2001, 40, 4729-4731. (h) Malitesta, C.; Losito, I.; Zambonin, P. G. Anal. Chem. 1999, 71, 1366-1370. (i) Parmpi, P.; Kofinas, P. Biomaterials 2004, 25, 1969-1973.
26. Studies on imprinting of sugar: (a) Mayes, A. G.; Andersson, L. I.; Mosbach, K. Anal. Biochem. 1994, 222, 483-488. (b) Wulff, G.; Schauhoff, S. J. Org. Chem. 1991, 56, 395-400. (c) Wang, W.; Gao, S.; Wang, B. Org. Lett. 1999, 1, 1209-1212. (d) Striegler, S. Tetrahedron 2001, 57, 2349-2354. (e) Striegler, S. Macromolecules 2003, 36, 1310-1317. (f) Ishi-i, T.; Iguchi, R.; Shinkai, S. Tetrahedron 1999, 55, 3883-3892. (g) Friggeri, A.; Kobayashi, H.; Shinkai, S.; Reinhoudt, D. N. Angew. Chem., Int. Ed. 2001, 40, 4729-4731. (h) Malitesta, C.; Losito, I.; Zambonin, P. G. Anal. Chem. 1999, 71, 1366-1370. (i) Parmpi, P.; Kofinas, P. Biomaterials 2004, 25, 1969-1973.
27. Studies on imprinting of sugar: (a) Mayes, A. G.; Andersson, L. I.; Mosbach, K. Anal. Biochem. 1994, 222, 483-488. (b) Wulff, G.; Schauhoff, S. J. Org. Chem. 1991, 56, 395-400. (c) Wang, W.; Gao, S.; Wang, B. Org. Lett. 1999, 1, 1209-1212. (d) Striegler, S. Tetrahedron 2001, 57, 2349-2354. (e) Striegler, S. Macromolecules 2003, 36, 1310-1317. (f) Ishi-i, T.; Iguchi, R.; Shinkai, S. Tetrahedron 1999, 55, 3883-3892. (g) Friggeri, A.; Kobayashi, H.; Shinkai, S.; Reinhoudt, D. N. Angew. Chem., Int. Ed. 2001, 40, 4729-4731. (h) Malitesta, C.; Losito, I.; Zambonin, P. G. Anal. Chem. 1999, 71, 1366-1370. (i) Parmpi, P.; Kofinas, P. Biomaterials 2004, 25, 1969-1973.
28. Studies on imprinting of sugar: (a) Mayes, A. G.; Andersson, L. I.; Mosbach, K. Anal. Biochem. 1994, 222, 483-488. (b) Wulff, G.; Schauhoff, S. J. Org. Chem. 1991, 56, 395-400. (c) Wang, W.; Gao, S.; Wang, B. Org. Lett. 1999, 1, 1209-1212. (d) Striegler, S. Tetrahedron 2001, 57, 2349-2354. (e) Striegler, S. Macromolecules 2003, 36, 1310-1317. (f) Ishi-i, T.; Iguchi, R.; Shinkai, S. Tetrahedron 1999, 55, 3883-3892. (g) Friggeri, A.; Kobayashi, H.; Shinkai, S.; Reinhoudt, D. N. Angew. Chem., Int. Ed. 2001, 40, 4729-4731. (h) Malitesta, C.; Losito, I.; Zambonin, P. G. Anal. Chem. 1999, 71, 1366-1370. (i) Parmpi, P.; Kofinas, P. Biomaterials 2004, 25, 1969-1973.
29. p-Nitrophenyl pyranosides were chosen because octyl pyranosides lack chromophores. Although polymers were prepared in chloroform, acetonitrile was utilized in the rebinding tests due to the poor solubility of p-nitrophenyl pyranosides in chloroform.
30. 9a reported on p-nitrophenyl pyranoside imprinted polymers, MIP2 and NIP2 were prepared with much less MAA than that they had used.
31. Amounts of solution and polymer for these experiments were 2.0 mL and 15 mg, respectively. The nonimprinted polymer shows the same pattern of displacement isotherm.