Structure Revision of Similanamide to PF1171C by Total Synthesis

Yuichi Masuda; Ren Tanaka; A. Ganesan; Takayuki Doi

doi:10.1021/acs.jnatprod.5b00643

Structure Revision of Similanamide to PF1171C by Total Synthesis

Yuichi Masuda, Ren Tanaka, A. Ganesan, Takayuki Doi

PHA - Molecular Pharmaceutical Science

Research output: Contribution to journal › Article › peer-review

8 Citations (Scopus)

Abstract

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.

Original language	English
Pages (from-to)	2286-2291
Number of pages	6
Journal	Journal of Natural Products
Volume	78
Issue number	9
DOIs	https://doi.org/10.1021/acs.jnatprod.5b00643
Publication status	Published - 2015 Sep 25

ASJC Scopus subject areas

Analytical Chemistry
Molecular Medicine
Pharmacology
Pharmaceutical Science
Drug Discovery
Complementary and alternative medicine
Organic Chemistry

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abstract = "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.",

author = "Yuichi Masuda and Ren Tanaka and A. Ganesan and Takayuki Doi",

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AU - Masuda, Yuichi

AU - Tanaka, Ren

AU - Ganesan, A.

AU - Doi, Takayuki

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Y1 - 2015/9/25

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AB - 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.

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