Heptakis-6-amino-6-deoxy-β-cyclodextrin as a catalyst for H/D exchange

Tetrahedron Letters

Volumn 37, Issue 50, 1996, Pages 8963-8966

  Binder, Wolfgang H ^a   Menger, Fredric M ^a  

^a EMORY UNIVERSITY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

ACETALDEHYDE; BETA CYCLODEXTRIN DERIVATIVE; MALONIC ACID; PROTON; PYRUVIC ACID;

ARTICLE; CATALYSIS; CHEMICAL REACTION; REACTION ANALYSIS;

EID: 0030577477     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(96)02103-X     Document Type: Article

References (20)

1. 1. See for instance : Kresge, A. J.; Pure & Appl. Chem. 1991, Vol. 63, No 2, 213-221 and references therein.
2. 2. Selected examples : (a) Powers, V. M.; Koo, C. W.; Kenyon, G. L.; Gerlt, J. A.; Kozarich, J. W. Biochemistry 1991, 30, 9255-9263
3. (b) Stubbe J.; Abeles, R. H. Biochemistry 1980, 19, 5505-5512
4. (c) Neidhart, D. J.; Howell, P. L.; Petsko, G. A. Biochemistry 1991, 30, 9264-9273
5. (d) Xue, L.; Talalay, P.; Mildvan, A. S. Biochemistry 1990, 29, 7491-7500.
6. 3. (a) Hine, J. Acc. Chem. Res. 1978, 11, 1-7.
7. (b) Hine, J.; Sinha, A. J. Org. Chem. 1984, 49, 2186-2190.
8. (c) Gerlt, J. A.; Kozarich, J. W.; Kenyon, G. L.; Gassman, P. G. J. Am. Chem. Soc. 1991, 113, 9667-9669.
9. (d) Zeng, B.; Pollack, R. M. J. Am. Chem. Soc. 1991, 113, 3838-3842.
10. 4. Fenniri, H.; Lehn, J.-M.; Marquis-Rigault, A. Angew. Chem. Int. Ed. Engl. 1996, 35, No 3, 337-339.
11. 5 (a) Compound 2 was synthesized according to the following literature : Ashton, P. R.; Koeniger, R.; Stoddart, J. F. J. Org. Chem. 1996, 61, 903-908.
12. (b) All compounds synthesized were shown to be identical with the corresponding literature data. All other compounds were purchased from Aldrich.
13. 6. The term "pD" used in this article always refers to the pH-meter reading without further correction. Refer to the following literature for further details : Glasoe, P. K; Long, F. A. J. Phys. Chem. 1960, 64, 188-190.
14. 7. This method yields k(obs) for the H/D exchange.
15. 8. The same effect was observed by Lehn et al. and is attributed to strong ion binding of the polycation to the dianion. See the following literature for further detail : Hosseini, M. W.; Kintzinger, J.-P.; Lehn, J.-M.; Zahidi, A. Helv. Chim. Acta, 1989, Vol. 72, 1078-1083.
16. 9. Job, A. Ann. Chim. (10th series) 1928, 9, 113-204.
17. 10. Basnak, I.; Farkas, J. Coll. Czech. Chem. Commun. 1975, 40, 1038-1042.
18. 11. Synthesis : Whistler, R. L. and Anisuzzaman, A. K. M.; in Methods in Carbohydrate Chemistry, Vol. VIII, 1980, Academic Press, (editors : Whistler, R. L. and BeMiller, J. N.); pp 229 and pp 297-299.
19. -1).
20. 13. Dietrich, B.; Hosseini, M. W.; Lehn J.-M.; Sessions, R. B. Helv. Chim. Acta 1983, 66, 1262-1278.