Synthesis and identification of an endogenous sperm activating and attracting factor isolated from eggs of the ascidian Ciona intestinalis; An example of nanomolar-level structure elucidation of novel natural compound

Tohru Oishi; Hiroshi Tsuchikawa; Michio Murata; Manabu Yoshida; Masaaki Morisawa

doi:10.1016/j.tet.2004.02.075

Synthesis and identification of an endogenous sperm activating and attracting factor isolated from eggs of the ascidian Ciona intestinalis; An example of nanomolar-level structure elucidation of novel natural compound

Tohru Oishi, Hiroshi Tsuchikawa, Michio Murata, Manabu Yoshida, Masaaki Morisawa

Research output: Contribution to journal › Article

20 Citations (Scopus)

Abstract

A sperm-activating and attracting factor (SAAF) was isolated from the eggs of the ascidian Ciona intestinalis, and its structure was deduced with only approximately 4 μg of the specimen. Based upon the proposed structure, two epimers were synthesized from chenodeoxycholic acid in 16 steps. Comparison between synthetic and natural compounds led to the unambiguous structure determination of SAAF to be (3R,4R,7R,25S)-3,4,7,26-tetrahydroxycholestane-3,26- disulfate. The synthetic pure specimen was also utilized to confirm that both sperm-activation and attraction were elicited by a single compound.

Original language	English
Pages (from-to)	6971-6980
Number of pages	10
Journal	Tetrahedron
Volume	60
Issue number	33
DOIs	https://doi.org/10.1016/j.tet.2004.02.075
Publication status	Published - Aug 9 2004
Externally published	Yes

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All Science Journal Classification (ASJC) codes

Biochemistry
Drug Discovery
Organic Chemistry

Cite this

Oishi, T., Tsuchikawa, H., Murata, M., Yoshida, M., & Morisawa, M. (2004). Synthesis and identification of an endogenous sperm activating and attracting factor isolated from eggs of the ascidian Ciona intestinalis; An example of nanomolar-level structure elucidation of novel natural compound. Tetrahedron, 60(33), 6971-6980. https://doi.org/10.1016/j.tet.2004.02.075

Synthesis and identification of an endogenous sperm activating and attracting factor isolated from eggs of the ascidian Ciona intestinalis; An example of nanomolar-level structure elucidation of novel natural compound. / Oishi, Tohru; Tsuchikawa, Hiroshi; Murata, Michio; Yoshida, Manabu; Morisawa, Masaaki.

In: Tetrahedron, Vol. 60, No. 33, 09.08.2004, p. 6971-6980.

Research output: Contribution to journal › Article

Oishi, T, Tsuchikawa, H, Murata, M, Yoshida, M & Morisawa, M 2004, 'Synthesis and identification of an endogenous sperm activating and attracting factor isolated from eggs of the ascidian Ciona intestinalis; An example of nanomolar-level structure elucidation of novel natural compound', Tetrahedron, vol. 60, no. 33, pp. 6971-6980. https://doi.org/10.1016/j.tet.2004.02.075

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10.1016/j.tet.2004.02.075