Determination of absolute stereochemistry, total synthesis, and evaluation of peptides from the myxomycete Physarum melleum.
The absolute stereochemistry of melleumin A (1) and B (2), novel peptide compounds isolated from the myxomycete Physarum melleum, was determined by synthesis of their segments and by a modified Mosher's method. Total synthesis of melleumin B (2) was achieved by a stereoselective method, which provided further evidence for all the absolute stereochemistries of melleumin B (2). The Wnt signal inhibitory activities of 2 and its 10R-epimer 19 were evaluated. Compound 19 showed moderate inhibition of Wnt signal transcription, which suggests that melleumin analogues might be useful as Wnt signal inhibitors.
Hanazawa
Shuwa
S
Graduate School of Pharmaceutical Sciences, Chiba University, Chiba 263-8522, Japan.
Arai
Midori A
MA
Li
Xiaofan
X
Ishibashi
Masami
M
D000818:Animals; D002851:Chromatography, High Pressure Liquid; D047630:Depsipeptides / Q000138:chemical synthesis / Q000737:chemistry*; D019906:Nuclear Magnetic Resonance, Biomolecular; D010804:Physarum / Q000737:chemistry* / Q000378:metabolism; D011487:Protein Conformation; D015800:Protozoan Proteins / Q000138:chemical synthesis / Q000737:chemistry*; D015398:Signal Transduction; D013237:Stereoisomerism; D051153:Wnt Proteins / Q000037:antagonists & inhibitors / Q000378:metabolism
D047630:Depsipeptides; D015800:Protozoan Proteins; D051153:Wnt Proteins; C539389:melleumin A; C539390:melleumin B