Structure Revision of Similanamide to PF1171C by Total Synthesis.
The total synthesis of the proposed structure of similanamide, a cyclic hexapeptide recently isolated from the marine sponge-associated fungus Aspergillus similanensis KUFA 0013, was achieved by solid-phase synthesis of a linear precursor and solution-phase macrolactamization. The NMR spectra of our synthetic final product were not identical to those of the isolated material and led us to conclude that similanamide is identical to PF1171C, a previously reported diastereomeric hexapeptide.
Graduate School of Pharmaceutical Sciences, Tohoku University , 6-3 Aza-Aoba, Aramaki, Aoba-ku, Sendai, Miyagi 980-8578, Japan.
Yuichi
Y
Masuda
Graduate School of Pharmaceutical Sciences, Tohoku University , 6-3 Aza-Aoba, Aramaki, Aoba-ku, Sendai, Miyagi 980-8578, Japan.
Ren
R
Tanaka
School of Pharmacy, University of East Anglia , Norwich Research Park, Norwich NR4 7TJ, United Kingdom.
A
A
Ganesan
Graduate School of Pharmaceutical Sciences, Tohoku University , 6-3 Aza-Aoba, Aramaki, Aoba-ku, Sendai, Miyagi 980-8578, Japan.
Takayuki
T
Doi
D000818:Animals; D008386:Marine Biology; D015394:Molecular Structure; D019906:Nuclear Magnetic Resonance, Biomolecular; D010456:Peptides, Cyclic / Q000737:chemistry*; D011161:Porifera / Q000737:chemistry*; D060327:Solid-Phase Synthesis Techniques
C000599757:PF1171C; D010456:Peptides, Cyclic