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
N1 - Funding Information:
This work was supported in part by Grants-in-Aid for Scientific Research (No. 11558079) and Scientific Research on Priority Areas (A) (No. 12045235) from the Ministry of Education, Culture, Sports, Science and Technology, Japan. We are indebted to Wako Pure Chemical Industries, Ltd, and Banyu Pharmaceutical Co., Ltd, for their financial support. We thank Professors R. Noyori and M. Kitamura (COE, Nagoya University) for allowing us to use the NMR instruments. We also thank Dr T. Matsumoto (Nagoya University) for the measurement of the fluorescent X-ray analysis.
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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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 -