Relative and absolute configuration of versipelostatin, a down-regulator of molecular chaperone GRP78 expression
Relative and absolute configuration of versipelostatin, a down-regulator of molecular chaperone GRP78 expression
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DOI：
10.1021/ol070042t
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发表时间：
2007-04-12
期刊：
影响因子：
5.2
通讯作者：
Shin-Ya, Kazuo
中科院分区：
文献类型：
--
作者：
Park, Hae-Ryong;Chijiwa, Shuhei;Shin-Ya, Kazuo
Versipelostatin是第一种在应激条件下特异性抑制GRP 78表达和由此产生的强烈细胞死亡的化合物，与正常条件下的弱细胞毒性相反。Versipelostatin由具有α-酰基替窗酸和三个糖部分的大环糖苷配基组成。利用NMR技术确定糖苷配基部分的相对和绝对构型为4S、5S、6 R、9 S、10 S、13 S、16 R、18 R、19 R、20 R、24 R、27 R和29 S。
Versipelostatin is the first compound which specifically inhibits the expression of GRP78 and the resultant robust cell death under stress conditions, in contrast to the weak cytotoxicity under normal conditions. Versipelostatin consists of a macrocyclic aglycone with an alpha-acyltetronic acid and three sugar moieties. The relative and absolute configuration of the aglycone moiety was established to be 4S, 5S, 6R, 9S, 10S, 13S, 16R, 18R, 19R, 20R, 24R, 27R, and 29S utilizing NMR techniques.