Phosphoryl transfer enzymes and hypervalent phosphorus chemistry

Accounts of Chemical Research

Volumn 37, Issue 10, 2004, Pages 746-753

  Holmes, Robert R ^a,b,c,d,e,f  

^a UNIVERSITY OF MASSACHUSETTS   (United States)

^b Illinois Institute of Technology ^*

^c ILLINOIS INSTITUTE OF TECHNOLOGY   (United States)

^d PURDUE UNIVERSITY   (United States)

^e Carnegie Institute of Technology   (United States)

^f LUCENT TECHNOLOGIES   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

ANION; PHOSPHORUS; PHOSPHORYLASE; PHOSPHOTRANSFERASE;

ANION TRANSPORT; ARTICLE; BIOTRANSFORMATION; ENZYME ACTIVE SITE; ENZYME ACTIVITY; ENZYME MECHANISM; ENZYME SUBSTRATE; HYDROGEN BOND; MOLECULAR INTERACTION;

LACTOCOCCUS LACTIS; PHOSPHOGLUCOMUTASE; PHOSPHORUS; PHOSPHOTRANSFERASES (PHOSPHOMUTASES); PROTEIN BINDING;

EID: 6944229601     PISSN: 00014842     EISSN: None     Source Type: Journal    
DOI: 10.1021/ar040053b     Document Type: Article

References (74)

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17. For an excellent discussion of phosphoryl and acyl transfer reaction mechanisms based on the use of isotope effects, see. Cleland, W. W.; Hengge, A. C. Mechanisms of Phosphoryl and Acyl Transfer. FASEB J. 1995, 9, 1585-1594.
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19. Chandrasekaran, A.; Day, R. O.; Holmes, R. R. Coordination of Carbonyl and Carboxyl Oxygen Atoms with Phosphorus in the Presence of Hydrogen Bonding. P-O Donor Action. Inorg. Chem. 2001, 40, 6229-6238.
20. Chandrasekaran, A.; Day, R. O.; Holmes, R. RP-O Donor Action From Carboxylate Anions with Phosphorus in the Presence of Hydrogen Bonding. A Model for Phosphoryl Transfer Enzymes. Inorg. Chem. 2002, 41, 1645-1651.
21. Pimental, G. C.; McClellan, A. L. The Hydrogen Bond; W. H. Freeman and Co.: San Francisco, 1960.
22. th ed.; Harper Collins: New York, 1993, Appendix E.
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24. Chandrasekaran, A.; Sood, P.; Day, R. O.; Holmes, R. R. Chloro and Fluoro Substituted Phosphites, Phosphates, and Phosphoranes Exhibiting Sulfur and Oxygen Coordination. Inorg. Chem. 1999, 38, 3369-3376.
25. Chandrasekaran, A.; Day, R. O.; Holmes, R. R. Isomeric Intraconversions Among Penta- and Hexa-Coordinate Cyclic Oxyphosphoranes via Oxygen Atom Coordination. J. Am. Chem. Soc. 1997, 119, 11434-11441.
26. Chandrasekaran, A.; Day, R. O.; Holmes, R. R. Sulfonyl Containing Eight-Membered Rings Varying in Ring Conformation in Oxyphosphoranes. Hexacoordination vs Pentacoordination. Inorg. Chem. 1997, 36, 2578-2585.
27. Timosheva, N. V.; Chandrasekaran, A.; Day, R. O.; Holmes, R. R. Three-, Four-, and Five-Coordinate Phosphorus Compounds Containing Salicylate Ligands. Inorg. Chem. 1998, 37, 3862-3867.
28. Sherlock, D. J.; Chandrasekaran, A.; Day, R. O.; Holmes, R. R. Pentacoordination and Pseudopentacoordination via Sulfur Donor Action in Cyclic Phosphates and Phosphites. Inorg. Chem. 1997, 36, 5082-5089.
29. Prakasha, T. K.; Day, R. O.; Holmes, R. R. Diequatorial and Axial-Equatorial Orientations of Eight-Membered Rings in Monocyclic Pentaoxyphosphoranes Containing Trifluoroethoxy Groups. Inorg. Chem. 1992, 31, 1913-1921.
30. Prakasha, T. K.; Day, R. O.; Holmes, R. R. Conformational Variation of Sulfur-Bridged Eight-Membered Rings in Four-, Five-, and Six-Coordinated Oxygen Ligated Phosphorus Compounds. Inorg. Chem. 1992, 31, 3391-3397.
31. Prakasha, T. K.; Day, R. O.; Holmes, R. R. Influence of Phosphorus-Sulfur Bonding in the Formation of Octahedrally Coordinated Cyclic Pentaoxyphosphoranes. J. Am. Chem. Soc. 1993, 115, 2690-2695.
32. Holmes, R. R.; Prakasha, T. K.; Day, R. O. Eight-Membered Rings in Pentaoxyphosphoranes Containing Trifluoroethoxy Groups. Influence of P-S Bonding. Phosphorus, Sulfur, Silicon Relat. Elem. 1993, 75, 249-252.
33. Holmes, R. R.; Prakasha, T. K.; Day, R. O. Variations in Sulfur Containing Eight-Membered Ring Conformations of Hydrogen Bonded and Nonhydrogen Bonded Cyclic Phosphates and Octahedrally Coordinated Cyclic Pentaoxyphosphoranes. Inorg. Chem. 1993, 32, 4360-4367.
34. Sherlock, D. J.; Chandrasekaran, A.; Day, R. O.; Holmes, R. R. Hexacoordination via Sulfur Donor Action in Nitrogen and Chlorine Bonded Bicyclic Tetraoxyphosphoranes. J. Am. Chem. Soc. 1997, 119, 1317-1322.
35. Sherlock, D. J.; Chandrasekaran, A.; Prakasha, T. K.; Day, R. O.; Holmes, R. R. Conformational Preferences and Donor Atom Interaction Leading to Hexacoordination vs Pentacoordination in Bicyclic Tetraoxyphosphoranes. Inorg. Chem. 1998, 37, 93-101.
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37. Sood, P.; Chandrasekaran, A.; Day, R. O.; Holmes, R. R. Increased Coordination via Sulfur Donor Action in Cyclic Pentaoxyphosphoranes and the Parent Cyclic Phosphite. Influence of Pentafluorophenoxy Ligands. Inorg. Chem. 1998, 37, 3747-3752.
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39. Timosheva, N. V.; Chandrasekaran, A.; Day, R. O.; Holmes, R. R. Cyclic Three-, Four-, Five-, and Six-Coordinate Nitrogen Containing Phosphorus Compounds Varying in Size from Five- to Ten-Membered. Inorg. Chem. 1998, 37, 4945-4952.
40. Chandrasekaran, A.; Timosheva, N. V.; Day, R. O.; Holmes, R. R. Crystal Structures of Tris(8-dimethylaminonaphthyl)phosphane and its Hydrochloride Salt. The First Seven-Coordinate Phosphorus Compound. Inorg. Chem. 2000, 39, 1338-1339.
41. Chandrasekaran, A.; Day, R. O.; Holmes, R. R. Synthesis and Structure of Cyclic Phosphate, Phosphoramidate, Phosphonates, and Phosphonium Salts. Phosphatrane Formation. Inorg. Chem. 2000, 39, 5683-5689.
42. (a) Timosheva, N. V.; Chandrasekaran, A.; Day, R. O.; Holmes, R. R. Conversion of Tricoordinate to Hexacoordinate Phosphorus. Formation of a Phosphorane-Phosphatrane System. J. Am. Chem. Soc. 2002, 124, 7035-7040.
43. 31P NMR that intermolecular P(V) ↔ P(VI) equilibria are established in solution. For example, Schmidpeter, A.; von Criegern, T.; Blanck, K. Z. Naturforsch. 1976, 31b, 1058-1063 and references therein; Burgada, R.; Setton, R. The Chemistry of Organophosphorus Compounds; Hartley, F. R., Ed.; Wiley: New York, 1994; Vol.3, Chapter 3 and references therein;
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