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

10 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

UN SDGs

This output contributes to the following UN Sustainable Development Goals (SDGs)

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10.1021/acs.jnatprod.5b00643

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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",

note = "Publisher Copyright: {\textcopyright} 2015 The American Chemical Society and American Society of Pharmacognosy.",

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AU - Masuda, Yuichi

AU - Tanaka, Ren

AU - Ganesan, A.

AU - Doi, Takayuki

PY - 2015/9/25

Y1 - 2015/9/25

N2 - 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.

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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JF - Journal of Natural Products

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Structure Revision of Similanamide to PF1171C by Total Synthesis

Abstract

ASJC Scopus subject areas

UN SDGs

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