Synthesis of monofluoro- and difluoro- methylenephosphonate analogues of sn-glycerol-3-phosphate as substrates for glycerol-3-phosphate dehydrogenase and the X-ray structure of the fluoromethylenephosphonate moiety

Tetrahedron

Volumn 52, Issue 1, 1996, Pages 165-176

  Nieschalk, Jens ^a   Batsanov, Andrei S ^a   O'Hagan, David ^a   Howard, Judith A K ^a  

^a DURHAM UNIVERSITY   (United Kingdom)

Author keywords

[No Author keywords available]

Indexed keywords

GLYCEROL 3 PHOSPHATE DEHYDROGENASE; ORGANOFLUORINE DERIVATIVE; PHOSPHONIC ACID DERIVATIVE;

CONFERENCE PAPER; DRUG STRUCTURE; DRUG SYNTHESIS; ENZYME SPECIFICITY; FLUORINATION; METHODOLOGY; PRIORITY JOURNAL; X RAY FLUORESCENCE;

EID: 0029655735     PISSN: 00404020     EISSN: None     Source Type: Journal    
DOI: 10.1016/0040-4020(95)00890-K     Document Type: Article

References (38)

1. Engel, R. Chem. Rev., 1977, 77, 349;
2. G.M. Blackburn, Chem. Ind. (London), 1981, 134;
3. Blackburn, G.M.; Perrée, T. D.; Rashid, A.; Bisbal, C.; Lebleu, B.Chem. Scr., 1986, 26, 21.
4. Adams, P.R.; Harrison, R. Biochem. J., 1974, 141, 729.
5. Blackburn, G.M.; Kent, D.E. J. Chem. Soc., Chem. Commun., 1981, 511.
6. Gordeev, M.F.; Patel, D.V.; Barker, P.L; Gordon, E.M. Tetrahedron Lett., 1994, 35, 7585;
7. Hebel, D.; Kirk, K.L.; Kinjo, J.; Kovács, T.; Lesiak, K.; Baizarini, J.; De Clercq, E.; Torrence, P.F. Bioorg. Med. Chem. Lett., 1991, 1, 357;
8. Blackburn, G.M.; Kent, D.E.; Kolkmann, F. J. Chem Soc., Perkin Trans. 1., 1984, 1119.
9. Blackburn, G.M.; Kent, D.E. J. Chem. Soc., Perkin Trans. 1., 1986, 913.
10. Thatcher, G. R. J.; Campbell, A.S. J. Org. Chem., 1993, 58, 2272.
11. (a) Chambers, R.D.; Jaouhari, R.; O'Hagan, D. J. Chem. Soc., Chem. Commun., 1988, 1169.
12. (b) Chambers, R.D.; Jaouhari, R.; O'Hagan, D. Tetrahedron, 1989, 45, 5101.
13. Cheng, P.-J.; Hickey, R.; Engel, R.; Tropp, B.E. Biochim. Biophys. Acta., 1974, 341, 85.
14. Kraut, J. Acta Crystallogr., 1961, 14, 1146.
15. Okaya, Y. Acta Crystallogr., 1966, 20, 712.
16. Chambers, R.D.; O'Hagan, D.; Lamot, B.; Jain, S.C. J. Chem. Soc., Chem. Commun., 1990, 1053.
17. Some of these results have been communicated, Nieschalk, J.; O'Hagan, D. J. Chem. Soc., Chem. Commun., 1995, 719.
18. Differding, D,; Duthaler, R.O.; Krieger, A.; Rüegg, G.M.; Schmit, C. Synlett, 1991, 395;
19. McKenna, C.E.; Shen, P. J. Org. Chem., 1981, 46, 4573;
20. Blackburn, G.M.; England, D.A.; Kolkmann, F. J. Chem. Soc., Chem. Commun., 1981, 930;
21. Blackburn, G.M.; Brown, D.; Martin, S.J.; Parratt, M.J. J. Chem. Soc., Perkin Trans. 1., 1987, 181.
22. Gryszkiewicz-Trochimowski, E. Bull. Soc. Chim. Fr., 1967, 11, 4286;
23. Blackburn, G.M.; Parratt, M.J. J. Chem. Soc., Perkin Trans. 1., 1986, 1425.
24. Burton, D.J.; Flynn, R.M. Synthesis, 1979, 615.
25. Patois, C.; Savignac, P. J. Chem. Soc., Chem. Commun., 1993, 1711.
26. Burton, D.J.; Flynn, R.M., J. Fluorine Chem., 1977, 10, 329.
27. Elie, C.J.J.; Brounts, D.M.; Dreef, C.E.; van der Marel, G.A.; van Boom, J.H. Recl. Trav. Chim. Pays-Bas, 1992, 111, 192.
28. Obayashi, M.; Kondo, K. Tetrahedron Lett., 1982, 23, 2327.
29. For another preparation of 15 see: Obayashi, M.; Ito, E.; Matsui, K.; Kondo, K. Tetrahedron Lett., 1982, 23, 2323.
30. Hertel, L.W.; Grossmann, C.S.; Kroin, J.S. Synth. Commun., 1991, 21, 515.
31. Martin, S.F.; Dean, D.W.; Wagman, A.S. Tetrahedron Lett., 1992, 33, 1839.
32. Böhme, H.; Hartke, K. Chem. Ber., 1960, 93, 1305.
33. Halazy, S.; Ehrhard, A.; Danzin, C. J. Am. Chem. Soc., 1991, 113, 315.
34. Burke, T.R.; Smyth, M.S.; Otaka, A.; Nomizu, M.; Roller, P.R.; Wolf, G.; Case, R.; Shoelson, S.E. Biochemistry, 1994, 33, 6490.
35. Florini, J.R.; Vestling, C.S. Biochim. Biophys. Acta., 1957, 25, 575.
36. Cosier, J.; Glaser, A.M. J. Appl. Crystallogr., 1986, 19, 105.
37. Sheldrick, G.M. Acta. Crystallogr. Sect. A., 1990, 46, 467.
38. Sheldrick, G.M. SHELXL-93: Program for the refinement of crystal structures, University of Göttingen, Germany, 1994.