Structures of fibrostatins, new inhibitors of prolyl hydroxylase.
The structures of six inhibitors of prolyl hydroxylase, fibrostatins A, B, C, D, E and F produced by a strain of Streptomyces, were deduced to be 1, 2, 3, 4, 5 and 6, respectively, from chemical and spectroscopic evidence, especially from extensive 13C NMR studies including selective decoupling and low power selective decoupling experiments monitored by 13C-1H long-range couplings. These compounds are the first naturally occurring 2,6,7- or 3,6,7-tri-substituted or 2,3,6,7-tetra-substituted 5-hydroxy-1,4-naphthoquinone inhibitors possessing N-acetyl-L-cystein-S-yl moieties in the molecule.
Ohta
K
K
Central Research Division, Takeda Chemical Industries, Ltd., Osaka, Japan.
Kasahara
F
F
Ishimaru
T
T
Wada
Y
Y
Kanamaru
T
T
Okazaki
H
H
D003545:Cysteine / Q000031:analogs & derivatives*; D009682:Magnetic Resonance Spectroscopy; D008958:Models, Molecular; D009285:Naphthoquinones; D011393:Procollagen-Proline Dioxygenase / Q000037:antagonists & inhibitors*; D013302:Streptomyces / Q000032:analysis; D013329:Structure-Activity Relationship
D009285:Naphthoquinones; C058033:fibrostatin C; D011393:Procollagen-Proline Dioxygenase; D003545:Cysteine