Structural determination of stevastelins, novel depsipeptides from Penicillium sp.
Structures of novel immunosuppressants, stevastelin A, B and B3(1) were determined by their spectroscopic and chemical studies. Three stevastelins were shown to be cyclic depsipeptides composed of a fatty acid and three amino acid moieties. The sequence of these moieties was determined to be as 3,5-dihydroxy-2,4-dimethylstearylvalylthreonyl (or O-sulfonylthreonyl in stevastelin A)-O-acetylserine. Cyclic structures were shown to be formed by ester linkages between the carboxylic group of the O-acetylserine moiety and the 5-hydroxy group of the fatty acid moiety in stevastelin A and B, and the 3-hydroxy group of the fatty acid moiety in stevastelin B3.
Morino
T
T
Research and Development Division, Nippon Kayaku Co., Ltd., Tokyo, Japan.
Shimada
K
K
Masuda
A
A
Yamashita
N
N
Nishimoto
M
M
Nishikiori
T
T
Saito
S
S
D000900:Anti-Bacterial Agents / Q000737:chemistry*; D047630:Depsipeptides; D005656:Fungal Proteins; D007166:Immunosuppressive Agents / Q000737:chemistry*; D009682:Magnetic Resonance Spectroscopy; D015394:Molecular Structure; D010407:Penicillium; D010455:Peptides
D000900:Anti-Bacterial Agents; D047630:Depsipeptides; D005656:Fungal Proteins; D007166:Immunosuppressive Agents; D010455:Peptides; C100705:stevastelin B; C100706:stevastelin B3; C100704:stevastelin A