Catalysis of phosphodiester transesterification by Cu(II)-terpyridine complexes with peripheral pendent base groups: Implications for the mechanism

Tetrahedron Letters

Volumn 38, Issue 7, 1997, Pages 1107-1110

  Liu, Shanghao ^a   Hamilton, Andrew D ^a  

^a UNIVERSITY OF PITTSBURGH   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

ORGANOPHOSPHATE;

ARTICLE; CATALYSIS; DRUG SYNTHESIS; ESTERIFICATION; IN VITRO STUDY; METHODOLOGY; MODEL; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; REACTION ANALYSIS; STEREOCHEMISTRY;

EID: 0031575563     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(96)02519-1     Document Type: Article

References (14)

1. (1) (a) Stern, M. K.; Bashkin, J. K.; Sall, E. D. J. Am. Chem. Soc. 1990, 112, 5357;
2. (b) Bashkin, J. K.; Frolova, E. I.; Sampath, U. J. Am. Chem. Soc. 1994, 116, 5981
3. (2) Linkletter, B.; Chin, J. Angew. Chem. Int. Ed. Engl. 1995, 34, 472.
4. (3) Gerlt, J. A. In Nucleuses, 2nd Ed.; Linn, S. M., Lloyd, R. S., Roberts, R. J., Eds.; Cold Spring Harbor Laboratory Press: New York, 1993; p 1-34.
5. (4) (a) Jubian, V.; Veronese, A.; Dixon, R. P.; Hamilton, A. D. Angew. Chem. Int. Ed. Engl. 1995, 34, 1237;
6. (b) Jubian, V.; Dixon, R. P.; Hamilton, A. D. J. Am. Chem. Soc. 1992, 114, 1120.
7. (5) Breslow, R.; Berger, D.; Huang, D.-L. J. Am. Chem. Soc. 1990, 112, 3686.
8. (6) A Cu(II)-bipyridine complex with pendent ammonium groups was recently reported to be active catalyst for hydrolysis of bis(p-nitrophenyl)phosphate: Kövári, E.; Heitker, J.; Krämer, R. J. Chem. Soc., Chem. Commun. 1994, 2019.
9. (7) HPNPP and other similar p-nitrophenyl phosphoesters are limited models for RNA because they do not bind well to natural ribonucleases. Furthermore, hydrolysis of p-nitrophenyl phosphoesters has less requirement for general acid catalysis. However, general base catalysis is required for hydrolysis of both p-nitrophenyl phosphoesters and RNA. See (a) Thompson, J. E.; Raines, R. T. J. Am. Chem. Soc. 1994, 116, 5467;
10. (b) Breslow, R.; Chapman, W. H. Jr. Proc. Natl. Acad. Sci. 1996, 93, 10018.
11. (8) Goodman, M. S.; Jubian, V.; Hamilton, A. D. Tetrahedron Lett. 1995, 36, 2551.
12. 5 calcd 347.2110, obsd 347.2108.
13. (10) Chu, F.; Smith, J.; Lynch, V. M.; Anslyn, E. V. Inorg. Chem. 1995, 34, 5689.
14. (11) Wall, M.; Hynes, R. C.; Chin, J. Angew. Chem. Int. Ed. Engl. 1993, 32, 1633.