Hedathiosulfonic acids A and B, novel thiosulfonic acids from the deep-sea urchin Echinocardium cordatum

Masaki Kita; Masami Watanabe; Noboru Takada; Kiyotake Suenaga; Kaoru Yamada; Daisuke Uemura

doi:10.1016/S0040-4020(02)00654-3

Hedathiosulfonic acids A and B, novel thiosulfonic acids from the deep-sea urchin Echinocardium cordatum

Masaki Kita, Masami Watanabe, Noboru Takada, Kiyotake Suenaga, Kaoru Yamada, Daisuke Uemura

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

9 Citations (Scopus)

Abstract

Hedathiosulfonic acids A and B were isolated from the deep-sea urchin Echinocardium cordatum and were determined to be novel 6-undecanethiosulfonic acids by 2D NMR, HRMS, and methylation reaction. The stereostructure of hedathiosulfonic acid A was determined by the analysis of its degradation product, a cyclic β-hydroxysulfone. Hedathiosulfonic acids exhibited acute toxicity. We carried out various model reactions of the olefinic compounds with thiosulfonic acids and proved that, as is the case with natural products, synthesized thiosulfonic acid possessing a carbon-carbon double bond was converted into β-hydroxysulfone in the presence of oxygen.

Original language	English
Pages (from-to)	6405-6412
Number of pages	8
Journal	Tetrahedron
Volume	58
Issue number	32
DOIs	https://doi.org/10.1016/S0040-4020(02)00654-3
Publication status	Published - 2002 Aug 5
Externally published	Yes

Keywords

Isolation
Model reaction
Natural thiosulfonic acid
Structure determination

ASJC Scopus subject areas

Biochemistry
Drug Discovery
Organic Chemistry

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title = "Hedathiosulfonic acids A and B, novel thiosulfonic acids from the deep-sea urchin Echinocardium cordatum",

abstract = "Hedathiosulfonic acids A and B were isolated from the deep-sea urchin Echinocardium cordatum and were determined to be novel 6-undecanethiosulfonic acids by 2D NMR, HRMS, and methylation reaction. The stereostructure of hedathiosulfonic acid A was determined by the analysis of its degradation product, a cyclic β-hydroxysulfone. Hedathiosulfonic acids exhibited acute toxicity. We carried out various model reactions of the olefinic compounds with thiosulfonic acids and proved that, as is the case with natural products, synthesized thiosulfonic acid possessing a carbon-carbon double bond was converted into β-hydroxysulfone in the presence of oxygen.",

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author = "Masaki Kita and Masami Watanabe and Noboru Takada and Kiyotake Suenaga and Kaoru Yamada and Daisuke Uemura",

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T1 - Hedathiosulfonic acids A and B, novel thiosulfonic acids from the deep-sea urchin Echinocardium cordatum

AU - Kita, Masaki

AU - Watanabe, Masami

AU - Takada, Noboru

AU - Suenaga, Kiyotake

AU - Yamada, Kaoru

AU - Uemura, Daisuke

PY - 2002/8/5

Y1 - 2002/8/5

N2 - Hedathiosulfonic acids A and B were isolated from the deep-sea urchin Echinocardium cordatum and were determined to be novel 6-undecanethiosulfonic acids by 2D NMR, HRMS, and methylation reaction. The stereostructure of hedathiosulfonic acid A was determined by the analysis of its degradation product, a cyclic β-hydroxysulfone. Hedathiosulfonic acids exhibited acute toxicity. We carried out various model reactions of the olefinic compounds with thiosulfonic acids and proved that, as is the case with natural products, synthesized thiosulfonic acid possessing a carbon-carbon double bond was converted into β-hydroxysulfone in the presence of oxygen.

AB - Hedathiosulfonic acids A and B were isolated from the deep-sea urchin Echinocardium cordatum and were determined to be novel 6-undecanethiosulfonic acids by 2D NMR, HRMS, and methylation reaction. The stereostructure of hedathiosulfonic acid A was determined by the analysis of its degradation product, a cyclic β-hydroxysulfone. Hedathiosulfonic acids exhibited acute toxicity. We carried out various model reactions of the olefinic compounds with thiosulfonic acids and proved that, as is the case with natural products, synthesized thiosulfonic acid possessing a carbon-carbon double bond was converted into β-hydroxysulfone in the presence of oxygen.

KW - Isolation

KW - Model reaction

KW - Natural thiosulfonic acid

KW - Structure determination

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