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 | |
| Publication status | Published - 2002 Aug 5 |
| Externally published | Yes |
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Keywords
- Isolation
- Model reaction
- Natural thiosulfonic acid
- Structure determination
ASJC Scopus subject areas
- Biochemistry
- Organic Chemistry
- Drug Discovery
Cite this
Hedathiosulfonic acids A and B, novel thiosulfonic acids from the deep-sea urchin Echinocardium cordatum. / Kita, Masaki; Watanabe, Masami; Takada, Noboru; Suenaga, Kiyotake; Yamada, Kaoru; Uemura, Daisuke.
In: Tetrahedron, Vol. 58, No. 32, 05.08.2002, p. 6405-6412.Research output: Contribution to journal › Article
}
TY - JOUR
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
UR - http://www.scopus.com/inward/record.url?scp=0037026009&partnerID=8YFLogxK
UR - http://www.scopus.com/inward/citedby.url?scp=0037026009&partnerID=8YFLogxK
U2 - 10.1016/S0040-4020(02)00654-3
DO - 10.1016/S0040-4020(02)00654-3
M3 - Article
AN - SCOPUS:0037026009
VL - 58
SP - 6405
EP - 6412
JO - Tetrahedron
JF - Tetrahedron
SN - 0040-4020
IS - 32
ER -