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 | |
| 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
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
}
TY - JOUR
T1 - 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
AU - Oishi, Tohru
AU - Tsuchikawa, Hiroshi
AU - Murata, Michio
AU - Yoshida, Manabu
AU - Morisawa, Masaaki
PY - 2004/8/9
Y1 - 2004/8/9
N2 - 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.
AB - 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.
UR - http://www.scopus.com/inward/record.url?scp=3242706203&partnerID=8YFLogxK
UR - http://www.scopus.com/inward/citedby.url?scp=3242706203&partnerID=8YFLogxK
U2 - 10.1016/j.tet.2004.02.075
DO - 10.1016/j.tet.2004.02.075
M3 - Article
AN - SCOPUS:3242706203
VL - 60
SP - 6971
EP - 6980
JO - Tetrahedron
JF - Tetrahedron
SN - 0040-4020
IS - 33
ER -