Structure of argifin, a new chitinase inhibitor produced by Gliocladium sp.-Reference-Cited by-同舟云学术

Structure of argifin, a new chitinase inhibitor produced by Gliocladium sp.

Published:2000-03 Issue:13 Volume:41 Page:2141-2143
ISSN:0040-4039
Container-title:Tetrahedron Letters
language:en
Short-container-title:Tetrahedron Letters

Author:

Shiomi Kazuro,Arai Noriko,Iwai Yuzuru,Turberg Andreas,Kölbl Heinz,Ōmura Satoshi

Publisher

Elsevier BV

Subject

Organic Chemistry,Drug Discovery,Biochemistry

Reference3 articles.

1. Londershausen, M.; Turberg, A.; Bieseler, B.; Lennartz, M.; Peter, M. G. Pestic. Sci. 1996, 48, 305–314.

2. Koga, D.; Isogai, A.; Sakuda, S.; Matsumoto, S.; Suzuki, A.; Kimura, S.; Ide, A. Agric. Biol. Chem. 1987, 51, 471–476.

3. NMR experiments were performed on a Varian Unity 400 spectrometer using D2O or H2O–D2O (4:1, for amino protons) as solvents. 1H NMR (400 MHz) δ 8.42 (1H, d, J=5, Asp 1 NH), 8.34 (1H, d, J=7, Arg α-NH), 8.10 (1H, d, J=6, Ala NH), 7.75 (1H, d, J=9, Asp 2 NH), 7.36 (2H, dd, J=7, 7, MePhe ε1, ε2), 7.29 (1H, dd, J=7, 7, MePhe ζ), 7.23 (2H, d, J=7, MePhe δ1, δ2), 6.99 (1H, br.s, MeCbm NH), 5.10 (1H, dd, J=11, 3, MePhe α), 4.49 (1H, dd, J=14, 3, Asp 2 α), 4.36 (1H, dd, J=12, 3, Asp 1 α), 4.34 (1H, dd, J=14, 2, Arg α), 4.18 (1H, q, J=7, Ala α), 3.14 (1H, dd, J=14, 3, MePhe β1), 3.06 (1H, m, MePhe β2), 3.01 (2H, m, Arg δ), 2.95 (1H, dd, J=17, 3, Asp 1 β1), 2.87 (3H, s, MePhe NMe), 2.79 (1H, dd, J=17, 12, Asp 1 β2), 2.76 (3H, s, MeCbm Me), 2.70 (1H, dd, J=14, 3, Asp 2 β1), 2.41 (1H, dd, J=14, 14, Asp 2 β2), 1.43 (1H, m, Arg γ1), 1.32 (3H, d, J=7, Ala β), 1.21 (1H, m, Arg γ2), 1.08 (1H, m, Arg β1), −0.43 (1H, m, Arg β2); 13C NMR (100 MHz) δ 178.3 (s, Asp 1 CO), 177.2 (s, Asp 2 CO), 175.2 (s, Ala CO), 174.2 (s, Arg CO), 172.2 (s, Asp 2 γ), 170.6 (s, MePhe CO), 170.5 (s, Asp 1 γ), 155.1 (s, MeCbm CO), 153.5 (s, Arg ζ), 137.6 (s, MePhe γ), 129.6 (d×2, MePhe δ1, δ2), 129.0 (d×2, MePhe ε1, ε2), 127.1 (d, MePhe ζ), 62.4 (d, MePhe α), 52.7 (d, Asp 1 α), 52.1 (d, Asp 2 α), 49.5 (d, Ala α), 48.6 (d, Arg α), 40.5 (t, Arg δ), 38.7 (t, Asp 2 β), 36.0 (t, Asp 1 β), 33.3 (t, MePhe β), 29.6 (q, MePhe NMe), 26.3 (t, Arg β), 26.0 (q, MeCbm Me), 23.9 (t, Arg γ), 16.6 (q, Ala β); 15N NMR (40 MHz) δ 133.6 (Ala NH), 128.5 (Asp 1 NH), 127.8 (Asp 2 NH), 125.7 (Arg α-NH), 122.5 (MePhe NMe), 86.3 (MeCbm NH).

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