2
394 Bull. Chem. Soc. Jpn., 74, No. 12 (2001)
Action of Peroxynitrite on Organic Molecules
d, J = 8.4 Hz), 6.88 (1H, d, J = 8.8 Hz), 3.7 (1H, m), 3.0 (2H, m).
195 (1993).
J. S. Beckman, T. W. Beckman, J. Chen, P. A. Marshall,
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C. Szabo and H. Ohshima, Nitric Oxide: Biol. Chem., 1,
373 (1997).
4
6
1
4
-Methyl-4-nitro-2,5-cyclohexadienone (9a):
H
NMR
2
(
(
D O) δ 7.22 (2H, d, J = 9.8 Hz), 6.31 (2H, d, J = 9.8 Hz), 1.82
2
1
3H, s); H NMR (CD
3
CN) δ 7.16 (2H, d, J = 9.6 Hz), 6.33 (2H,
3
d, J = 9.6 Hz), 1.88 (3H, s).
,1ꢀ-Dimethyl-4,4ꢀ-dioxo-1,1ꢀ,4,4ꢀ-tetrahydrobiphenyl (10a):
H NMR (D O) δ 6.96 (2H, d, J = 9.6 Hz), 6.07 (2H, d, J = 9.6
Hz), 1.34 (3H, s); H NMR (CD
.02 (2H, d, J = 9.6 Hz), 1.36 (3H, s).
,2ꢀ-Dihydroxy-5,5ꢀ-dimethylbiphenyl (11a):
1
4
L. J. Kennedy, K. Moore, J. L. Caulfield, S. R. Tannen-
1
2
baum, and P. C. Dedon, Chem. Res. Toxicol., 10, 1118 (1997).
1
3
CN) δ 6.92 (2H, d, J = 9.6 Hz),
5
(1999).
6
D. M. Kuhn and T. J. Geddes, J. Biol. Chem., 274, 29726
6
4
7
1
2
H
NMR
K. Takakura, J. S. Beckman, L. A. MacMillan-Crow, and J.
(
8
CDCl
3
) δ 7.11 (2H, d, J = 8.4 Hz), 7.07 (2H, s), 6.93 (2H, d, J =
P. Crow, Arch. Biochem. Biophys., 369, 197 (1999).
L. A. MacMillan-Crow and J. A. Thompson, Arch. Bio-
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M. Uppu, and W. A. Pryor, Arch. Biochem. Biophys., 345, 160
(1997).
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Wolin, J. Biol. Chem., 273, 32009 (1998).
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C. E. Cross, J. Biol. Chem., 273, 30255 (1998).
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Toxicol., 10, 1331 (1997).
.4 Hz), 2.30 (6H, s); CI-MS m/z (rel intensity) 215 (M+1, 100).
7
1
2
,6-Di-t-butyl-4-nitrophenol (13):
3
H NMR (CD CN) δ
7
1
.79 (2H, s), 1.31 (18H, s); CI-MS m/z (rel intensity) 252 (M+1,
00), 236 (9), 220 (5).
2
8
4
8
1
,6-Di-t-butyl-1,4-benzoquinone (14):
δ 6.47 (2H, s), 1.24 (18H, s); CI-MS m/z (rel intensity) 221 (M+1,
00).
,4ꢀ-Dihydroxy-3,3ꢀ,5,5ꢀ-tetra-t-butylbiphenyl (15):
NMR (CD CN) δ 7.29 (4H, s), 1.42 (36H, s); CI-MS m/z (rel in-
tensity) 410 (M , 100), 299 (52), 243 (44).
H NMR (CD
3
CN)
9
1
4
9
1
4
H
3
+
1
4
-Nitrocatechol (16): H NMR (D
2
O) δ 7.65 (1H, d, J = 8.8
Hz), 7.55 (1H, s), 6.60 (1H, d, J = 8.8 Hz).
5
0
1
N-Methyl-p-toluidine (18):
2
H NMR (D O) δ 7.00 (2H, d,
J = 8.4 Hz), 6.68 (2H, d, J = 8.4 Hz), 2.59 (3H, s), 2.09 (3H, s);
1
H NMR (CD
3
CN) δ 6.93 (2H, d, J = 8.4 Hz), 6.49 (2H, d, J =
8
(
.4 Hz), 2.70 (3H, s), 2.18 (3H, s); CI-MS m/z (rel intensity) 120
M−1, 100), 91 (70), 77 (60).
N-Methyl-N-nitroso-p-toluidine (19):
5
1
1
3
H NMR (CD CN)
δ 7.44 (2H, d, J = 8.4 Hz), 7.30 (2H, d, J = 8.4 Hz), 3.38 (3H, s),
.31 (3H, s); CI-MS m/z (rel intensity) 151 (M+1, 57), 122 (100).
2
5
2
1
N,N-Dimethyl-p-toluidine-N-oxide (20):
2
H NMR (D O)
δ 7.55 (2H, d, J = 8.4 Hz), 7.23 (2H, d, J = 8.4 Hz), 3.43 (6H, s),
1
2
.22 (3H, s); H NMR (CD
2H, d, J = 8.4 Hz), 3.60 (6H, s), 2.36 (3H, s); CI-MS m/z (rel in-
tensity) 150 (M−1, 100).
3
CN) δ 7.74 (2H, d, J = 8.4 Hz), 7.27
(
1
Benzotriazole (22): H NMR (CD CN) δ 7.82 (2H, dd, J =
.2, 3.2 Hz), 7.44 (2H, dd, J = 6.2, 3.2 Hz); MS m/z (rel intensity)
20 (M+1, 100).
Unidentified product (23): H NMR (CD
3
6
1
1
3
CN) δ 7.65 (1H, d, J
=
8.4 Hz), 7.15 (1H, t, J = 8.4 Hz), 6.82 (1H, d, J = 8.4 Hz), 6.69
(
1H, t, J = 8.4 Hz).
,3-Epoxy-2,3-dihydro-1,4-naphthoquinone (25):
NMR (CD CN) δ 7.94 (2H, dd, J = 5.6, 3.2 Hz), 7.82 (2H, dd, J
5.6, 3.2 Hz), 4.02 (2H, s); CI-MS m/z (rel intensity) 175 (M+1,
5
3
1
2
H
3
=
1
00%), 146 (23), 105 (35).
Acetophenone (27): H NMR (CD
.4 Hz), 7.5–7.6 (1H, m), 7.49 (2H, t, J = 8.4 Hz), 2.55 (3H, s).
trans-Stilbene Oxide (30): H NMR (CDCl
10H, m), 3.87 (2H, s).
Benzil (31): H NMR (CDCl
1
3
CN) δ 7.95 (2H, d, J =
23 S. Goldstein and G. Czapski, Nitric Oxide: Biol. Chem., 1,
417 (1997).
24 N. Nonoyama, K. Hisatome, C. Shoda, and H. Suzuki, Tet-
rahedron Lett., 40, 6939 (1999).
25 N. Nonoyama, K. Chiba, K. Hisatome, H. Suzuki, and F.
Shintani, Tetrahedron Lett., 40, 6933 (1999).
8
1
3
) δ 7.3–7.4
(
1
3
) δ 7.98 (4H, dd, J = 7.2, 1.5
Hz), 7.67 (2H, t, J = 7.2 Hz), 7.51 (4H, t, J =7.2 Hz).
2
6
H. Ischiropoulos, L. Zhu, J. Chen, M. Tsai, J. C. Martin, C.
This work was financially supported by a grant for Specially
Promoted Scientific Research (No. 08101003) and a grant (No.
D. Smith, and J. S. Beckman, Arch. Biochem. Biophys., 298, 431
(1992).
2
7
A. van der Vliet, J. P. Eiserich, C. A. O’Neill, B. Halliwell,
and C. E. Cross, Arch. Biochem. Biophys., 319, 341 (1995).
C. Daveu, C. Servy, M. Dendane, P. Marin, and C.
Ducrocq, Nitric Oxide: Biol. Chem., 1, 234 (1997).
F. Shintani, T. Kinoshita, S. Kanba, T. Ishikawa, E. Suzuki,
1
2640576) from the Ministry of Education, Science, Sports
and Culture. N.N. thanks the Japan Society for the Promotion
of Science for a Fellowship (No. 9191).
2
8
29
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