Synthesis and micellization of a long-chain β-hydroxyalkyl p- nitrophenyl phosphate

Tetrahedron Letters

Volumn 40, Issue 15, 1999, Pages 2867-2870

  Moss, Robert A ^a   Jiang, Weiguo ^a  

^a RUTGERS UNIVERSITY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

4 NITROPHENYL PHOSPHATE;

ARTICLE; CHEMICAL ANALYSIS; CHEMICAL REACTION; CHEMICAL STRUCTURE; MICELLE; SYNTHESIS;

EID: 0033537805     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(99)00354-8     Document Type: Article

References (31)

1. Brown, D.M.; Usher, D.A. J. Chem. Soc. 1965, 6558.
2. (a) Breslow, R.; Huang, D.-L.; Anslyn, E. Proc. Natl. Acad. Sci. USA 1989, 86, 1746.
3. (b) Breslow, R.; Huang, D.-L. Ibid. 1991, 88, 4080.
4. (c) Morrow, J.R.; Buttrey, L.A.; Berback, K.A. Inorg. Chem. 1992, 31, 16.
5. (d) Chin, K.O.A.; Morrow, J.R.; Ibid. 1994, 33, 5036.
6. (e) Whahnon, D.; Hynes, R.C.; Chin, J.K. Chem. Commun. 1994, 1441.
7. (f) Moss, R.A.; Bracken, K. Ibid. 1997, 563.
8. (g) Moss, R.A.; Zhang, J.; Bracken, K. Ibid. 1997, 1639.
9. (h) Moss, R.A.; Zhang, J.; Ragunathan, K.G. Tetrahedron Lett. 1998, 39, 1529.
10. (i) Baykal, U.; Akkaya, E.U. Ibid. 1998, 39, 5861.
11. (j) Dong, S.D.; Breslow, R. Ibid. 1998, 39, 9343.
12. (k) Molenveld, P.; Engbersen, J.F.J.; Kooijman, H; Spek, A.L.; Reinhoudt, D.N. J. Am. Chem. Soc. 1998, 120, 6726.
13. (a) Ellis, M.V.; James, S.R.; Perisic, O.; Downes, C.P.; Williams, R.L.; Katan, M. J. Biol. Chem. 1998, 273, 11650.
14. (b) Zhou, C.; Qian, X.; Roberts, M.F. Biochem. 1997, 36, 10089.
15. (c) Volwerk, J.J.; Filthuth, E.; Griffith, O.H.; Jain, M.K. Ibid. 1994, 33, 3464.
16. (d) Tan, C.A.; Roberts, M.F. Ibid. 1998, 37, 4275.
17. (e) Berg, O.G.; Rogers, J.; Yu, B.-Z.; Yao, J.; Romsted, L.S.; Jain, M.K. Ibid. 1997, 36, 14512.
18. For a related approach to cationic lipid derivatives of 1,2,4-butanetriol, see Ren, T.; Liu, D. Tetrahedron Lett. 1999, 40, 209.
19. Nagashima, N.; Ohno, M. Chem. Pharm. Bull. 1991, 39, 1972. Wagner, D.; Verheyden, J.P.H.; Moffatt, J.G. J. Org. Chem. 1974, 39, 24.
20. Nagashima, N.; Ohno, M. Chem. Pharm. Bull. 1991, 39, 1972. Wagner, D.; Verheyden, J.P.H.; Moffatt, J.G. J. Org. Chem. 1974, 39, 24.
21. Chattopadhyaya, J.B.; Reese, C.B. Tetrahedron Lett. 1979, 52, 5059.
22. 3 wash).
23. This method is a combination of related usages of pyridinium p-toluenesulfonate [Miyashita, M.; Yoshikoshi, A.; Grieco, P.A. J. Org. Chem. 1977, 42, 3772] and acidic ion exchange resins [Bongini, A.; Cardillo, G.; Orena, M.; Sandri, S. Synthesis 1979, 618].
24. This method is a combination of related usages of pyridinium p-toluenesulfonate [Miyashita, M.;Yoshikoshi, A.; Grieco, P.A. J. Org. Chem. 1977, 42, 3772] and acidic ion exchange resins [Bongini, A.; Cardillo, G.; Orena, M.; Sandri, S. Synthesis 1979, 618].
25. 13), 0.9 (t, 3H, Me). Anal. C,H,N,P.
26. Elworthy, P.H.; Florence, A.T.; Macfarlene, C.B. Solubilization by Surface Active Agents, London, Chapman and Hall, 1968, pp. 32f.
27. Conditions: pH 7.0, 0.01 M KCl, 37 °C. The release of p-nitrophenylate was spectroscopically monitored at 400 nm.
28. For lanthanide cleavages of HPNP (1), see references 2c,d,i. For leading references to cleavages of related phosphodiester substrates, see Roigk, A.; Hettich, R.; Schneider, H-J. Inorg. Chem. 1998, 37, 751.
29. Fendler, J.H.; Fendler, E.J. Catalysis in Micellar and Macromolecular Systems, New York, Academic Press, 1975.
30. Moss, R.A.; Park, B.D.; Scrimin, P.; Ghirlanda, G. Chem. Commun. 1995, 1627.
31. 3+] = 10[substrate].