Synthesis and characterization of α-phosphorylated ketones: Models for the molybdopterin precursor

Tetrahedron

Volumn 54, Issue 37, 1998, Pages 10973-10986

  Van Houten, Kelly A ^a   Boggs, Christine M ^a   Pilato, Robert S ^a  

^a Bldg 142   (United States)

Author keywords

NMR; Phosphates; Pyridines

Indexed keywords

KETONE; MOLYBDOPTERIN; PHOSPHATE; PTERIN DERIVATIVE; PYRIDINE DERIVATIVE; UNCLASSIFIED DRUG;

ARTICLE; MODEL; NUCLEAR MAGNETIC RESONANCE; PHOSPHORYLATION; PRIORITY JOURNAL; SYNTHESIS;

ACYTHOPEUS BURKHARTORUM; ACYTHOPEUS COCCINIAE; AGROMYZIDAE; AMICTIDES; AMICTIDES SIMILARIS; AMICTIDES SIMILIS; BARIS; BARIS HELLERI; BARIS PARVULA; BARIS PERRIERI; BARIS PILITARSIS; BARIS RIFTENSIS; CITRULLUS COLOCYNTHIS; CUCUMIS SATIVUS; DISTIGMA;

EID: 0032505189     PISSN: 00404020     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4020(98)00663-2     Document Type: Article

References (27)

1. [1] Hille, R. Chem. Rev. 1996, 96, 2757-2816.
2. [2] Pilato, R. S.; Steifel, E. I. Molybdenum and Tungsten Enzymes; Marcel Dekker, Inc.: New York, 1998, in press.
3. [3] Pilato, R. S.; Stiefel, E. I. Catalysis by Molybdenum-Cofactor Enzymes; Pilato, R. S.; Stiefel, E. I., Ed.; Marcel Dekker Inc: New York, 1993, pp 133-88.
4. [4] Molybdenum Enzymes Cofactors and Model Systems, developed from the symposium on the molybdenum enzymes, (Stiefel, E. I.; Coucouvanis, D.; Newton, W. E., Ed.); American Chemical Society: Washington DC, 1993; Vol. 535, pp 1-142.
5. [5] Pitterle, D. M.; Rajagopalan, K. V. J. Biol. Chem. 1993, 268, 13499-13505.
6. [6] Pitterle, D. M.; Johnson, J. L.; Rajagopalan, K. V. J. Biol. Chem. 1993, 268, 13506-9.
7. [7] Johnson, J. L.; Wuebbens, M. M.; Rajagopalan, K. V. J. Biol. Chem. 1989, 264, 13440-7.
8. [8] Wuebbens, M. M.; Rajagopalan, K. V. J. Biol. Chem. 1993, 268, 13493-8.
9. [9] Taylor, S.; Kluger, R. J. Am. Chem. Soc. 1993, 115, 867-71.
10. [10] Kluger, R.; Taylor, S. D. J. Am. Chem. Soc. 1991, 113, 996-1001.
11. [11] Dauben, W. G.; Hendricks, R. T.; Pandy, B.; Wu, S. C.; Zhang, X.; Luzzio, M. J. Tetrahedron Lett. 1995, 36, 2385-8.
12. [12] Crockett, G. C. Aldrichimica Acta 1983, 16, 47-56.
13. [13] Broka, C.; Hozumi, T.; Arentzen, R.; Itakurea, K. Nucl. Acids Res. 1980, 8, 5461-71.
14. [14] Reese, C. B. Tetrahedron 1978, 34, 3143-79.
15. [15] Reese, C. B.; Zard, L. Nucl. Acids Res. 1981, 9, 4611-26.
16. [16] Gallagher, M. J. Phosphourous-31 Spectroscopy in Stereochemical Analysis. (Quin, L.D.; Verkade, J.D., Eds.) VCH Publishers: Deerfield Beach, Fl, 1987, pp Chapter 11.
17. [17] Bentrude, W. G. Conformational Behavior of Six-Memebered Rings in the Stereochemical Analysis Series. (Juaristi, E., Ed.) VCH Publishers: New York, 1995, pp 245-93.
18. [18] Due to the proximity of resonances of H(4) and H(4′), the full decoupling of H(4) resulted in loss of coupling to H(4′).
19. [19] Unangst, P. C.; Connor, D. T. Heterocyclic Chem. 1992, 29, 1097-1100.
20. [20] Pilato, R.S., unpublished results.
21. [21] Caputo, R.; Ferreri, C.; Palumbo, G. Tetrahedron 1986, 42, 2369-76.
22. [22] Caputo, R.; Ferreri, C.; Palumbo, G. Synthesis 1991, 223-4.
23. [23] Van Houten, K. A.; Heath, D. C.; Barringer, C. A.; Rheingold, A. L.; Pilato, R. S. Inorg. Chem. 1998, Accepted for Publicaton.
24. [24] Hsu, J. K.; Bonangelino, C. J.; Kaiwar, S. P.; Boggs, C. M.; Fettinger, J. C.; Pilato, R. S. Inorg. Chem. 1996, 35, 4743-51.
25. [25] Kaiwar, S. P.; Hsu, J. K.; Liable-Sands, L. M.; Rheingold, A. L.; Pilato, R. S. Inorg. Chem. 1997, 36, 4234-40.
26. [26] Kaiwar, S. P.; Vodacek, A.; Blough, N. B.; Pilato, R. S. J. Am. Chem. Soc. 1997, 119, 9211-4.
27. [27] Davies, J. A.; Hartley, F. R.; Murray, S. G. J.C.S. Dalton 1979, 1705-8.