Verticilide: elucidation of absolute configuration and total synthesis.
Verticilide (1) is a 24-membered cyclic depsipeptide isolated from the culture broth of Verticillium sp. FKI-1033. It inhibits ryanodine binding to ryanodine receptor (RyR) and has insecticidal activity. The stereochemistry of 2-hydroxyheptanoic acid in verticilide was elucidated by chiral HPLC analysis of the degradation product 6 and synthetic (+) and (-)-6. We also describe the practical total synthesis of verticilide. [reaction: see text].
Monma
Souichi
S
Kitasato Institute for Life Sciences and Graduate School of Infection Control Sciences, Kitasato University, Tokyo 108-8641, Japan.
Sunazuka
Toshiaki
T
Nagai
Kenichiro
K
Arai
Takahiro
T
Shiomi
Kazuro
K
Matsui
Ryosuke
R
Omura
Satoshi
S
D001667:Binding, Competitive / Q000187:drug effects; D002851:Chromatography, High Pressure Liquid; D002855:Chromatography, Thin Layer; D047630:Depsipeptides / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology; D006863:Hydrogen-Ion Concentration; D007202:Indicators and Reagents; D009682:Magnetic Resonance Spectroscopy; D013058:Mass Spectrometry; D008958:Models, Molecular; D008968:Molecular Conformation; D012433:Ryanodine / Q000378:metabolism; D019837:Ryanodine Receptor Calcium Release Channel / Q000187:drug effects; D016339:Spectrometry, Mass, Fast Atom Bombardment; D013056:Spectrophotometry, Ultraviolet; D013237:Stereoisomerism; D020172:Verticillium / Q000737:chemistry
D047630:Depsipeptides; D007202:Indicators and Reagents; D019837:Ryanodine Receptor Calcium Release Channel; C522755:verticilide; D012433:Ryanodine