Catalysis by nitric oxide synthase

Current Opinion in Chemical Biology

Volumn 2, Issue 5, 1998, Pages 656-663

  Marletta, Michael A ^a,b   Hurshman, Amy R ^b   Rusche, Kristin M ^a  

^a UNIVERSITY OF MICHIGAN MEDICAL SCHOOL   (United States)

^b UNIVERSITY OF MICHIGAN   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

5,6,7,8-TETRAHYDROBIOPTERIN; ANTIOXIDANT; ARGININE; BIOPTERIN; CITRULLINE; DRUG DERIVATIVE; FLAVINE ADENINE NUCLEOTIDE; FLAVINE MONONUCLEOTIDE; HEME; HYDROGEN PEROXIDE; ISOENZYME; NITRIC OXIDE; NITRIC OXIDE SYNTHASE; TETRAHYDROBIOPTERIN;

BIOSYNTHESIS; CATALYSIS; CHEMISTRY; METABOLISM; REVIEW;

ANTIOXIDANTS; ARGININE; BIOPTERIN; CATALYSIS; CITRULLINE; FLAVIN MONONUCLEOTIDE; FLAVIN-ADENINE DINUCLEOTIDE; HEME; HYDROGEN PEROXIDE; ISOENZYMES; NITRIC OXIDE; NITRIC OXIDE SYNTHASE;

EID: 0032176803     PISSN: 13675931     EISSN: None     Source Type: Journal    
DOI: 10.1016/S1367-5931(98)80098-7     Document Type: Article

References (50)

1. Nathan C: Nitric oxide as a secretory product of mammalian cells. FASEB J 1992, 6:3051-3064.
2. Moncada S, Palmer RM, Higgs EA: Nitric oxide: physiology, pathophysiology, and pharmacology. Pharmacol Rev 1991, 43:109-142.
3. Marietta MA: Nitric oxide synthase structure and mechanism. J Biol Chem 1993, 268:12231-12234.
4. Marietta MA: Nitric oxide synthase: aspects concerning structure and catalysis. Cell 1994, 78:927-930.
5. Stuehr DJ, Griffith OW: Mammalian nitric oxide synthases. Adv Enzymol Relat Areas Mol Biol 1992, 65:287-346.
6. Pollock JS, Forstermann U, Mitchell JA, Warner TD, Schmidt HH, Nakane M, Murad F: Purification and characterization of particulate endothelium-derived relaxing factor synthase from cultured and native bovine aortic endothelial cells. Proc Natl Acad Sci USA 1991, 88:10480-10484.
7. Lamas S, Marsden PA, Li GK, Tempst P, Michel T: Endothelial nitric oxide synthase: molecular cloning and characterization of a distinct constitutive enzyme isoform. Proc Natl Acad Sci USA 1992, 89:6348-6352.
8. Busconi L, Michel T: Endothelial nitric oxide synthase. N-terminal myrisoylation determines subcellular localization. J Biol Chem 1993, 268:8410-8413.
9. Liu J, Sessa WC: Identification of covalently bound amino-terminal myristic acid in endothelial nitric oxide synthase. J Biol Chem 1994, 269:11691-11694.
10. Liu J, Garcia-Cardena G, Sessa WC: Biosynthesis and palmitoylation of endothelial nitric oxide synthase: mutagenesis of palmitoylation sites, cysteines-15 and/or -26, argues against depalmitoylation-induced translocation of the enzyme. Biochemistry 1995, 34:12333-12340.
11. Bredt DS, Hwang PM, Glatt CE, Lowenstein C, Reed RR, Snyder SH: Cloned and expressed nitric oxide synthase structurally resembles cytochrome P-450 reductase. Nature 1991, 351:714-718.
12. Brenman JE, Chao DS, Gee SH, McGee AW, Craven SE, Santillano DR, Wu Z, Huang F, Xia H, Peters MF, Froehner SC, Bredt DS: Interaction of nitric oxide synthase with the postsynaptic density protein PSD-95 and alpha1 -syntrophin mediated by PDZ domains. Cell 1996, 84:757-767.
13. Hevel JM, White KA, Marietta MA: Purification of the inducible murine macrophage nitric oxide synthase: identification as a flavoprotein and detection of enzyme-bound tetrahydrobiopterin. In The Biology of Nitric Oxide: 2. Enzymology, Biochemistry and Immunology. Edited by Moncada S, Marietta MA, Hibbs Jr JB, Higgs EA. London: Portland Press; 1992:19-21.
14. Stuehr DJ, Cho HJ, Kwon NS, Weise MF, Nathan CF: Purification and characterization of the cytokine-induced macrophage nitric oxide synthase: an FAD- and FMN-containing flavoprotein. Proc Natl Acad Sci USA 1991, 88:7773-7777.
15. Cho HJ, Xie Q-W, Calaycay J, Mumford RA, Swiderek KM, Lee TD, Nathan C: Calmodulin is a subunit of nitric oxide synthase from macrophages. J Exp Med 1992, 176:599-604.
16. Stevens-Truss R, Marietta MA: Interaction of calmodulin with the inducible murine macrophage nitric oxide synthase. Biochemistry 1995, 34:15638-15645.
17. Silvagno F, Xia H, Bredt DS: Neuronal nitric-oxide synthase-mu, an alternatively spliced isoform expressed in differentiated skeletal muscle. J Biol Chem 1996, 271:11204-11208.
18. Magee T, Fuentes AM, Garban H, Rajavashisth T, Marquez D, Rodriguez JA, Rajfer J, Gonzalez-Cadavid NF: Cloning of a novel neuronal nitric oxide synthase expressed in penis and lower urinary tract. Biochem Biophys Res Commun 1996, 226:145-151.
19. Iyengar R, Stuehr DJ, Marietta MA: Macrophage synthesis of nitrite, nitrate, and N-nitrosamines: precursors and role of the respiratory burst. Proc Nat/Acad Sci USA 1987, 84:6369-6373.
20. Stuehr DJ, Kwon NS, Nathan CF, Griffith OW, Feldman PL, Wiseman J: N omega-hydroxy-L-arginine is an intermediate in the biosynthesis of nitric oxide from L-arginine. J Biol Chem 1991, 266:6259-6263.
21. Pufahl RA, Nanjappan PG, Woodard RW, Marietta MA: Mechanistic probes of N-hydroxylation of L-arginine by the inducible nitric oxide synthase from murine macrophages. Biochemistry 1992, 31:6822-6828.
22. 15N-NMR study of tautomers in N-monosubstituted amidines in N, N-diphenylgnanidine.
23. Tayeh MA, Marietta MA: Macrophage oxidation of L-arginine to nitric oxide, nitrite, and nitrate. Tetrahydrobiopterin is required as a cofactor. J Biol Chem 1989, 264:19654-19658.
24. Kwon NS, Nathan CF, Stuehr DJ: Reduced biopterin as a cofactor in the generation of nitrogen oxides by murine macrophages. J Biol Chem 1989, 264:20496-204501.
25. Kaufman S: The phenylalanine hydroxylating system. Adv Enzymol Relat Areas Mol Biol 1993, 67:77-264.
26. Rodriguez-Crespo I, Gerber NC, Ortiz de Montellano PR: Endothelial nitric-oxide synthase. Expression in Escherichia coli, spectroscopic characterization, and role of tetrahydrobiopterin in dimer formation. J Biol Chem 1996, 271:11462-11467.
27. Vermilion JL, Coon MJ: Identification of the high and low potential flavins of liver microsomal NADPH-cytochrome P-450 reductase. J Biol Chem 1978, 253:8812-8819.
28. Narhi LO, Fulco AJ: Characterization of a catalytically self-sufficient 119,000-dalton cytochrome P-450 monooxygenase induced by barbiturates in Bacillus megaterium. J Biol Chem 1986, 261:7160-7169.
29. Narhi LO, Fulco AJ: Identification and characterization of two functional domains in cytochrome P-450BM-3, a catalytically self-sufficient monooxygenase induced by barbiturates in Bacillus megaterium. J Biol Chem 1987, 262:6683-6690.
30. White KA, Marietta MA: Nitric oxide synthase is a cytochrome P-450 type hemoprotein. Biochemistry 1992, 31:6627-6631.
31. Richards MK, Marietta MA: Characterization of neuronal nitric oxide synthase and a C415H mutant, purified from a baculovirus overexpression system. Biochemistry 1994, 33:14723-14732.
32. Richards MK, Clague MJ, Marietta MA: Characterization of C415 mutants of neuronal nitric oxide synthase. Biochemistry 1996, 35:7772-7780.
33. Wang J, Stuehr DJ, Ikeda-Saito M, Rousseau DL: Heme coordination and structure of the catalytic site in nitric oxide synthase. J Biol Chem 1993, 268:22255-22258.
34. Crane BR, Arvai AS, Gachhui R, Wu C, Ghosh DK, Getzoff ED, Stuehr DJ, Tainer JA: The structure of nitric oxide synthase oxygenase domain and inhibitor complexes. Science 1997, 278:425-431.
35. Perry JM, Marietta MA: The effect of transition metals on nitric oxide synthase catalysis. Proc Natl Acad Sci USA 1998, in press. This key paper describes the effect of transition metals on NOS activity. In particular, the paper shows that NOS is isolated with bound transition metals (copper and zinc), however, only reconstitution with iron leads to active enyzme. Copper and other transition metals are inhibitory. This apparent role for a nonheme iron has important mechanistic ramifications.
36. Abu-Soud HM, Yoho LL, Stuehr DJ: Calmodulin controls neuronal nitric-oxide synthase by a dual mechanism. J Biol Chem 1994, 269:32047-32050.
37. Abu-Soud HM, Feldman PL, Clark P, Stuehr DJ: Electron transfer in the nitric-oxide synthases. J Biol Chem 1994, 269:32318-32326.
38. Perry JM, Moon N, Zhao Y, Dunham WR, Marietta MA: EPR characterization of the flavin semiquinone radical in nitric oxide synthase. Chem Biol 1998, 5:355-364.
39. 4B is hydrogen bonded to the propionic acid carboxylate of ring A in porphyrin. This seems to place the pterin too far away to directly participate in the chemistry of the reaction. Bound pterin interacts with residues of both subunits, and may thereby stabilize the dimeric form of the enzyme.
40. G-hydroxy- L-arginine by nitric oxide synthase: evidence for the involvement of the heme in catalysis. Biochem Biophys Res Commun 1993, 193:963-970.
41. ω-hydroxy- L-arginine by nitric oxide synthase. Biochemistry 1995, 34:1930-1941.
42. δ-cyanoomithine as an alternate product in the peroxide shunt-catalyzed NOS reaction. Besides providing additional mechanistic insight into the reaction, this paper showed that L-arginine is not a substrate in this variant of the reaction (shown in [41]), supporting the view that the heme is not involved in the conversion of L-arginine to L-NHA.
43. -, no conclusion can be reached concerning whether the reaction is a two- or three-electron oxidation.
44. Gerber NC, Nishida CR, Ortiz de Montellano PR: Characterization of human liver inducible nitric oxide synthase expressed in Escherichia coli. Arch Biochem Biophys 1997, 343:249-253.
45. Presta A, Siddhanta U, Wu C, Sennequier N, Huang L, Abu-Soud HM, Erzurum S, Stuehr DJ: Comparative functioning of dihydro- and tetrahydropterins in supporting electron transfer, catalysis, and subunit dimerization in inducible nitric oxide synthase. Biochemistry 1998, 37:298-310.
46. -. This suggests a role for the pterin the second step of the reaction. Also, this form of the enzyme did not catalyze a reaction with L-arginine, again consistent with the noninvolvement of heme in the first step of the reaction.
47. 4B decreases the lifetime of the complex and may, therefore, influence the course of the reaction by affecting electron transfer.
48. Hufton SE, Jennings IG, Cotton RG: Structure and function of the aromatic amino acid hydroxylases. Biochem J 1995, 311:353-366.
49. Kappock TJ, Caradonna JP: Pterin-dependent amino-acid hydroxylases. Chem Rev 1996, 96:2659-2756.
50. Klatt P, Schmid M, Leopold E, Schmidt K, Werner ER, Mayer B: The pteridine binding site of brin nitric oxide synthase. Tetrahydrobiopterin binding kinetics, specificity, and allosteric interaction with the substrate domain. J Biol Chem 1994, 269:13861-13866.