Amino acid derivatives of β-cyclodextrin

Journal of Organic Chemistry

Volumn 61, Issue 3, 1996, Pages 903-908

  Ashton, Peter R ^a   Königer, Rainer ^a   Stoddart, J Fraser ^a   Alker, David ^b   Harding, Valerie D ^b  

^a UNIVERSITY OF BIRMINGHAM   (United Kingdom)

^b PFIZER GLOBAL RESEARCH AND DEVELOPMENT   (United Kingdom)

Author keywords

[No Author keywords available]

Indexed keywords

AMINO ACID DERIVATIVE; BETA CYCLODEXTRIN DERIVATIVE;

ARTICLE; DRUG SYNTHESIS; REACTION ANALYSIS;

EID: 0030024976     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo951396d     Document Type: Article

References (68)

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33. Coupling of the side chain of a protected glutamic acid to per-6-amino-β-cyclodextrin (4) in an analogous synthesis was attempted and afforded a crude product, from which it was not possible to separate and characterize the expected derivative. The coupling reaction between 4 and N-Boc-glutamic acid α-benzyl ester is believed not to have gone to completion on account of the steric bulk of the protecting groups preventing exhaustive amide coupling at the 6-position of the cyclodextrin.
34. Further studies showed that nucleophilic displacement of iodide anions from per-6-iodo-β-cyclodextrin, employing poorer nucleophiles or elevated temperatures, favors the intramolecular substitution reaction, resulting in the formation of 3,6-anhydro-D-glucopyranose residues within the structure of per-6-iodo-β-cyclodextrin. See: Fujita, K.; Tahara, T.; Egashira, Y.; Yamamura, H.; Imoto, T.; Koga, T.; Fujioka, T.; Mihashi, K. Chem. Lett. 1988, 705-708. Fujita, K.; Yamamura, H.; Imoto, T.; Fujioka, T.; Mihashi, K. J. Org. Chem. 1988, 53, 1943-1947. Fujita, K.; Egashira, Y.; Tahara, T.; Imoto, T.; Koga, T. Tetrahedron Lett. 1989, 30, 1285-1288. Fujita, K.; Tahara, T ; Koga, T. Chem. Lett. 1989, 821-824. Fujita, K.: Tahara, T.; Yamamura, H.; Imoto, T.; Koga, T.; Fujioka, T.; Mihashi, K. J. Org. Chem. 1990, 55, 877-880. Yamamura, H.; Fujita, K. Chem. Pharm. Bull. 1991, 39, 2505-2508. Gadelle, A.; Defaye, J. Angew. Chem., Int. Ed. Engl. 1991, 30, 78-80. Ashton, P. R.; Ellwood, P.: Staton, I.; Stoddart, J. F. Angew. Chem., Int. Ed. Engl. 1991, 30. 80-81. Ashton, P. R.: Ellwood, P.: Staton, I.; Stoddart, J. F J. Org. Chem. 1991, 56, 7274-7280. Yamamura, H.; Ezaka, T.; Kawase, Y.; Kawai, M.; Butsugan, Y.; Fujita, K. J. Chem. Soc , Chem. Commun. 1993, 636-637.
35. Further studies showed that nucleophilic displacement of iodide anions from per-6-iodo-β-cyclodextrin, employing poorer nucleophiles or elevated temperatures, favors the intramolecular substitution reaction, resulting in the formation of 3,6-anhydro-D-glucopyranose residues within the structure of per-6-iodo-β-cyclodextrin. See: Fujita, K.; Tahara, T.; Egashira, Y.; Yamamura, H.; Imoto, T.; Koga, T.; Fujioka, T.; Mihashi, K. Chem. Lett. 1988, 705-708. Fujita, K.; Yamamura, H.; Imoto, T.; Fujioka, T.; Mihashi, K. J. Org. Chem. 1988, 53, 1943-1947. Fujita, K.; Egashira, Y.; Tahara, T.; Imoto, T.; Koga, T. Tetrahedron Lett. 1989, 30, 1285-1288. Fujita, K.; Tahara, T ; Koga, T. Chem. Lett. 1989, 821-824. Fujita, K.: Tahara, T.; Yamamura, H.; Imoto, T.; Koga, T.; Fujioka, T.; Mihashi, K. J. Org. Chem. 1990, 55, 877-880. Yamamura, H.; Fujita, K. Chem. Pharm. Bull. 1991, 39, 2505-2508. Gadelle, A.; Defaye, J. Angew. Chem., Int. Ed. Engl. 1991, 30, 78-80. Ashton, P. R.; Ellwood, P.: Staton, I.; Stoddart, J. F. Angew. Chem., Int. Ed. Engl. 1991, 30. 80-81. Ashton, P. R.: Ellwood, P.: Staton, I.; Stoddart, J. F J. Org. Chem. 1991, 56, 7274-7280. Yamamura, H.; Ezaka, T.; Kawase, Y.; Kawai, M.; Butsugan, Y.; Fujita, K. J. Chem. Soc , Chem. Commun. 1993, 636-637.
36. Further studies showed that nucleophilic displacement of iodide anions from per-6-iodo-β-cyclodextrin, employing poorer nucleophiles or elevated temperatures, favors the intramolecular substitution reaction, resulting in the formation of 3,6-anhydro-D-glucopyranose residues within the structure of per-6-iodo-β-cyclodextrin. See: Fujita, K.; Tahara, T.; Egashira, Y.; Yamamura, H.; Imoto, T.; Koga, T.; Fujioka, T.; Mihashi, K. Chem. Lett. 1988, 705-708. Fujita, K.; Yamamura, H.; Imoto, T.; Fujioka, T.; Mihashi, K. J. Org. Chem. 1988, 53, 1943-1947. Fujita, K.; Egashira, Y.; Tahara, T.; Imoto, T.; Koga, T. Tetrahedron Lett. 1989, 30, 1285-1288. Fujita, K.; Tahara, T ; Koga, T. Chem. Lett. 1989, 821-824. Fujita, K.: Tahara, T.; Yamamura, H.; Imoto, T.; Koga, T.; Fujioka, T.; Mihashi, K. J. Org. Chem. 1990, 55, 877-880. Yamamura, H.; Fujita, K. Chem. Pharm. Bull. 1991, 39, 2505-2508. Gadelle, A.; Defaye, J. Angew. Chem., Int. Ed. Engl. 1991, 30, 78-80. Ashton, P. R.; Ellwood, P.: Staton, I.; Stoddart, J. F. Angew. Chem., Int. Ed. Engl. 1991, 30. 80-81. Ashton, P. R.: Ellwood, P.: Staton, I.; Stoddart, J. F J. Org. Chem. 1991, 56, 7274-7280. Yamamura, H.; Ezaka, T.; Kawase, Y.; Kawai, M.; Butsugan, Y.; Fujita, K. J. Chem. Soc , Chem. Commun. 1993, 636-637.
37. Further studies showed that nucleophilic displacement of iodide anions from per-6-iodo-β-cyclodextrin, employing poorer nucleophiles or elevated temperatures, favors the intramolecular substitution reaction, resulting in the formation of 3,6-anhydro-D-glucopyranose residues within the structure of per-6-iodo-β-cyclodextrin. See: Fujita, K.; Tahara, T.; Egashira, Y.; Yamamura, H.; Imoto, T.; Koga, T.; Fujioka, T.; Mihashi, K. Chem. Lett. 1988, 705-708. Fujita, K.; Yamamura, H.; Imoto, T.; Fujioka, T.; Mihashi, K. J. Org. Chem. 1988, 53, 1943-1947. Fujita, K.; Egashira, Y.; Tahara, T.; Imoto, T.; Koga, T. Tetrahedron Lett. 1989, 30, 1285-1288. Fujita, K.; Tahara, T ; Koga, T. Chem. Lett. 1989, 821-824. Fujita, K.: Tahara, T.; Yamamura, H.; Imoto, T.; Koga, T.; Fujioka, T.; Mihashi, K. J. Org. Chem. 1990, 55, 877-880. Yamamura, H.; Fujita, K. Chem. Pharm. Bull. 1991, 39, 2505-2508. Gadelle, A.; Defaye, J. Angew. Chem., Int. Ed. Engl. 1991, 30, 78-80. Ashton, P. R.; Ellwood, P.: Staton, I.; Stoddart, J. F. Angew. Chem., Int. Ed. Engl. 1991, 30. 80-81. Ashton, P. R.: Ellwood, P.: Staton, I.; Stoddart, J. F J. Org. Chem. 1991, 56, 7274-7280. Yamamura, H.; Ezaka, T.; Kawase, Y.; Kawai, M.; Butsugan, Y.; Fujita, K. J. Chem. Soc , Chem. Commun. 1993, 636-637.
38. Further studies showed that nucleophilic displacement of iodide anions from per-6-iodo-β-cyclodextrin, employing poorer nucleophiles or elevated temperatures, favors the intramolecular substitution reaction, resulting in the formation of 3,6-anhydro-D-glucopyranose residues within the structure of per-6-iodo-β-cyclodextrin. See: Fujita, K.; Tahara, T.; Egashira, Y.; Yamamura, H.; Imoto, T.; Koga, T.; Fujioka, T.; Mihashi, K. Chem. Lett. 1988, 705-708. Fujita, K.; Yamamura, H.; Imoto, T.; Fujioka, T.; Mihashi, K. J. Org. Chem. 1988, 53, 1943-1947. Fujita, K.; Egashira, Y.; Tahara, T.; Imoto, T.; Koga, T. Tetrahedron Lett. 1989, 30, 1285-1288. Fujita, K.; Tahara, T ; Koga, T. Chem. Lett. 1989, 821-824. Fujita, K.: Tahara, T.; Yamamura, H.; Imoto, T.; Koga, T.; Fujioka, T.; Mihashi, K. J. Org. Chem. 1990, 55, 877-880. Yamamura, H.; Fujita, K. Chem. Pharm. Bull. 1991, 39, 2505-2508. Gadelle, A.; Defaye, J. Angew. Chem., Int. Ed. Engl. 1991, 30, 78-80. Ashton, P. R.; Ellwood, P.: Staton, I.; Stoddart, J. F. Angew. Chem., Int. Ed. Engl. 1991, 30. 80-81. Ashton, P. R.: Ellwood, P.: Staton, I.; Stoddart, J. F J. Org. Chem. 1991, 56, 7274-7280. Yamamura, H.; Ezaka, T.; Kawase, Y.; Kawai, M.; Butsugan, Y.; Fujita, K. J. Chem. Soc , Chem. Commun. 1993, 636-637.
39. Further studies showed that nucleophilic displacement of iodide anions from per-6-iodo-β-cyclodextrin, employing poorer nucleophiles or elevated temperatures, favors the intramolecular substitution reaction, resulting in the formation of 3,6-anhydro-D-glucopyranose residues within the structure of per-6-iodo-β-cyclodextrin. See: Fujita, K.; Tahara, T.; Egashira, Y.; Yamamura, H.; Imoto, T.; Koga, T.; Fujioka, T.; Mihashi, K. Chem. Lett. 1988, 705-708. Fujita, K.; Yamamura, H.; Imoto, T.; Fujioka, T.; Mihashi, K. J. Org. Chem. 1988, 53, 1943-1947. Fujita, K.; Egashira, Y.; Tahara, T.; Imoto, T.; Koga, T. Tetrahedron Lett. 1989, 30, 1285-1288. Fujita, K.; Tahara, T ; Koga, T. Chem. Lett. 1989, 821-824. Fujita, K.: Tahara, T.; Yamamura, H.; Imoto, T.; Koga, T.; Fujioka, T.; Mihashi, K. J. Org. Chem. 1990, 55, 877-880. Yamamura, H.; Fujita, K. Chem. Pharm. Bull. 1991, 39, 2505-2508. Gadelle, A.; Defaye, J. Angew. Chem., Int. Ed. Engl. 1991, 30, 78-80. Ashton, P. R.; Ellwood, P.: Staton, I.; Stoddart, J. F. Angew. Chem., Int. Ed. Engl. 1991, 30. 80-81. Ashton, P. R.: Ellwood, P.: Staton, I.; Stoddart, J. F J. Org. Chem. 1991, 56, 7274-7280. Yamamura, H.; Ezaka, T.; Kawase, Y.; Kawai, M.; Butsugan, Y.; Fujita, K. J. Chem. Soc , Chem. Commun. 1993, 636-637.
40. Further studies showed that nucleophilic displacement of iodide anions from per-6-iodo-β-cyclodextrin, employing poorer nucleophiles or elevated temperatures, favors the intramolecular substitution reaction, resulting in the formation of 3,6-anhydro-D-glucopyranose residues within the structure of per-6-iodo-β-cyclodextrin. See: Fujita, K.; Tahara, T.; Egashira, Y.; Yamamura, H.; Imoto, T.; Koga, T.; Fujioka, T.; Mihashi, K. Chem. Lett. 1988, 705-708. Fujita, K.; Yamamura, H.; Imoto, T.; Fujioka, T.; Mihashi, K. J. Org. Chem. 1988, 53, 1943-1947. Fujita, K.; Egashira, Y.; Tahara, T.; Imoto, T.; Koga, T. Tetrahedron Lett. 1989, 30, 1285-1288. Fujita, K.; Tahara, T ; Koga, T. Chem. Lett. 1989, 821-824. Fujita, K.: Tahara, T.; Yamamura, H.; Imoto, T.; Koga, T.; Fujioka, T.; Mihashi, K. J. Org. Chem. 1990, 55, 877-880. Yamamura, H.; Fujita, K. Chem. Pharm. Bull. 1991, 39, 2505-2508. Gadelle, A.; Defaye, J. Angew. Chem., Int. Ed. Engl. 1991, 30, 78-80. Ashton, P. R.; Ellwood, P.: Staton, I.; Stoddart, J. F. Angew. Chem., Int. Ed. Engl. 1991, 30. 80-81. Ashton, P. R.: Ellwood, P.: Staton, I.; Stoddart, J. F J. Org. Chem. 1991, 56, 7274-7280. Yamamura, H.; Ezaka, T.; Kawase, Y.; Kawai, M.; Butsugan, Y.; Fujita, K. J. Chem. Soc , Chem. Commun. 1993, 636-637.
41. Further studies showed that nucleophilic displacement of iodide anions from per-6-iodo-β-cyclodextrin, employing poorer nucleophiles or elevated temperatures, favors the intramolecular substitution reaction, resulting in the formation of 3,6-anhydro-D-glucopyranose residues within the structure of per-6-iodo-β-cyclodextrin. See: Fujita, K.; Tahara, T.; Egashira, Y.; Yamamura, H.; Imoto, T.; Koga, T.; Fujioka, T.; Mihashi, K. Chem. Lett. 1988, 705-708. Fujita, K.; Yamamura, H.; Imoto, T.; Fujioka, T.; Mihashi, K. J. Org. Chem. 1988, 53, 1943-1947. Fujita, K.; Egashira, Y.; Tahara, T.; Imoto, T.; Koga, T. Tetrahedron Lett. 1989, 30, 1285-1288. Fujita, K.; Tahara, T ; Koga, T. Chem. Lett. 1989, 821-824. Fujita, K.: Tahara, T.; Yamamura, H.; Imoto, T.; Koga, T.; Fujioka, T.; Mihashi, K. J. Org. Chem. 1990, 55, 877-880. Yamamura, H.; Fujita, K. Chem. Pharm. Bull. 1991, 39, 2505-2508. Gadelle, A.; Defaye, J. Angew. Chem., Int. Ed. Engl. 1991, 30, 78-80. Ashton, P. R.; Ellwood, P.: Staton, I.; Stoddart, J. F. Angew. Chem., Int. Ed. Engl. 1991, 30. 80-81. Ashton, P. R.: Ellwood, P.: Staton, I.; Stoddart, J. F J. Org. Chem. 1991, 56, 7274-7280. Yamamura, H.; Ezaka, T.; Kawase, Y.; Kawai, M.; Butsugan, Y.; Fujita, K. J. Chem. Soc , Chem. Commun. 1993, 636-637.
42. Further studies showed that nucleophilic displacement of iodide anions from per-6-iodo-β-cyclodextrin, employing poorer nucleophiles or elevated temperatures, favors the intramolecular substitution reaction, resulting in the formation of 3,6-anhydro-D-glucopyranose residues within the structure of per-6-iodo-β-cyclodextrin. See: Fujita, K.; Tahara, T.; Egashira, Y.; Yamamura, H.; Imoto, T.; Koga, T.; Fujioka, T.; Mihashi, K. Chem. Lett. 1988, 705-708. Fujita, K.; Yamamura, H.; Imoto, T.; Fujioka, T.; Mihashi, K. J. Org. Chem. 1988, 53, 1943-1947. Fujita, K.; Egashira, Y.; Tahara, T.; Imoto, T.; Koga, T. Tetrahedron Lett. 1989, 30, 1285-1288. Fujita, K.; Tahara, T ; Koga, T. Chem. Lett. 1989, 821-824. Fujita, K.: Tahara, T.; Yamamura, H.; Imoto, T.; Koga, T.; Fujioka, T.; Mihashi, K. J. Org. Chem. 1990, 55, 877-880. Yamamura, H.; Fujita, K. Chem. Pharm. Bull. 1991, 39, 2505-2508. Gadelle, A.; Defaye, J. Angew. Chem., Int. Ed. Engl. 1991, 30, 78-80. Ashton, P. R.; Ellwood, P.: Staton, I.; Stoddart, J. F. Angew. Chem., Int. Ed. Engl. 1991, 30. 80-81. Ashton, P. R.: Ellwood, P.: Staton, I.; Stoddart, J. F J. Org. Chem. 1991, 56, 7274-7280. Yamamura, H.; Ezaka, T.; Kawase, Y.; Kawai, M.; Butsugan, Y.; Fujita, K. J. Chem. Soc , Chem. Commun. 1993, 636-637.
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67. Lear, J. D.; Wasserman, Z. R.; DeGrado, W. F. Science 1988, 240, 1177-1181; Science 1989, 243, 622-628. Sasaki, T.; Kaiser, E. T. J. Am. Chem. Soc. 1989, 111, 380-381. Mutter, M.; Vuilleumier, S. Angew. Chem., Int. Ed. Engl. 1989, 28, 535-554. Mutter, M.; Tuchscherer, G. G.; Miller, C.; Altmann, K.-H.; Carey, R. I.; Wyss, D. F.; Labhardt, A. M.; Rivier, J. E. J. Am. Chem. Soc. 1992, 114, 1463-1470. Hahn, K. W.; Klis W. A.; Stewart, J. M. Science 1990, 248, 1544-1547. Ghadiri, M. R.; Soares, C.; Choi, C. J. Am. Chem. Soc. 1992, 114, 825-831. Ghadiri, M. R.; Soares, C ; Choi, C. J. Am. Chem. Soc. 1992, 114, 4000-4002. Ghadiri, M. R.; Case, M. A. Angew. Chem., Int. Ed. Engl. 1993, 32, 1594-1597.
68. Lear, J. D.; Wasserman, Z. R.; DeGrado, W. F. Science 1988, 240, 1177-1181; Science 1989, 243, 622-628. Sasaki, T.; Kaiser, E. T. J. Am. Chem. Soc. 1989, 111, 380-381. Mutter, M.; Vuilleumier, S. Angew. Chem., Int. Ed. Engl. 1989, 28, 535-554. Mutter, M.; Tuchscherer, G. G.; Miller, C.; Altmann, K.-H.; Carey, R. I.; Wyss, D. F.; Labhardt, A. M.; Rivier, J. E. J. Am. Chem. Soc. 1992, 114, 1463-1470. Hahn, K. W.; Klis W. A.; Stewart, J. M. Science 1990, 248, 1544-1547. Ghadiri, M. R.; Soares, C.; Choi, C. J. Am. Chem. Soc. 1992, 114, 825-831. Ghadiri, M. R.; Soares, C ; Choi, C. J. Am. Chem. Soc. 1992, 114, 4000-4002. Ghadiri, M. R.; Case, M. A. Angew. Chem., Int. Ed. Engl. 1993, 32, 1594-1597.