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
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
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DOI：
10.1016/j.tet.2004.02.075
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发表时间：
2004-08-09
期刊：
影响因子：
2.1
通讯作者：
Morisawa, M
中科院分区：
文献类型：
--
作者：
Oishi, T;Tsuchikawa, H;Morisawa, M
从海鞘幼虫的卵中分离到一种精子激活和吸引因子(SAAF)，仅用4杯左右的标本就可推测其结构。根据所提出的结构，以鹅去氧胆酸为原料，经16步反应合成了两个异构体。将合成化合物与天然化合物进行比较，确定其结构为(3R，4R，7R，25S)-3，4，7，26-tetrahydroxycholestane-3，26-disulfate.人工合成的纯标本也被用来证实单一化合物既能激活精子又能吸引精子。(C)2004爱思唯尔有限公司。保留所有权利。
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 mug 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. (C) 2004 Elsevier Ltd. All rights reserved.