SYNTHESIS OF AN INHIBITOR OF SPHINGOSINE-1-PHOSPHATE LYASE
SYNTHESIS OF AN INHIBITOR OF SPHINGOSINE-1-PHOSPHATE LYASE
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DOI：
10.1016/s0040-4039(00)75971-5
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发表时间：
1994-02-07
影响因子：
1.8
通讯作者：
MILLER, SPF
中科院分区：
文献类型：
--
作者：
BOUMENDJEL, A;MILLER, SPF
合成了2-乙烯基二氢鞘氨醇-1-磷酸1，并测试了其对鞘氨醇-L-磷酸裂解酶的抑制作用。通过甲硫氨酸亚胺与N-甲氧基-N-甲基棕榈酰胺的酰化反应制备了碳骨架。乙烯基团是通过热亚砜消除而生成的。羰基还原和去保护得到2-乙烯基二氢鞘氨醇。以双(2-氰乙基)-N，N-二异丙基亚磷酰胺为单功能亚磷酸化试剂引入磷酸基团。
The 2-vinyl dihydrosphingosine-1-phosphate 1 was synthesized and tested for inhibition of sphingosine-l-phosphate lyase. The carbon skeleton was prepared by acylation of a methionine imine with N-methoxy-N-methyl palmitamide. The vinyl group was generated by thermal sulfoxide elimination. Reduction of both carbonyl groups and deprotection gave 2-vinyl dihydrosphingosine. The phosphate group was introduced by means of bis(2-cyanoethyl)-N,N-diisopropyl-phosphoramidite as monofunctional phosphitylation reagent.