Stereocontrolled synthesis and investigation of the biosynthetic transformations of 16(S),17(S)-epoxy-PDn-3 DPA.
Stereocontrolled synthesis and investigation of the biosynthetic transformations of 16(S),17(S)-epoxy-PDn-3 DPA.
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16(S),17(S)-epoxy-PDn-3 DPA 的立体控制合成和生物合成转化研究。
DOI：
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发表时间：
2017
影响因子：
3.2
通讯作者：
A. Vik
中科院分区：
文献类型：
--
作者：
K. G. Primdahl;J. Tungen;P. R. S. De Souza;R. Colas;Jesmond Dalli;T. Hansen;A. Vik
pd1n - 3dpa是一种特殊的促溶解脂质介质，具有有效的抗炎特性和促溶解生物活性。这些天然存在的化合物是目前生物分子化学和药物发现的兴趣所在。为了研究环氧化合物中间体在n-3二十碳五烯酸生物合成pd1n - 3dpa中的作用，采用立体选择性全合成法制备了环氧酸16(S),17(S)-环氧- pdn - 3dpa，本文命名为epdn - 3dpa。epdn - 3dpa的合成材料允许研究其在pd1n - 3dpa的生物合成中的作用。结果表明，中性粒细胞以epdn - 3dpa为中间体合成pd1n - 3dpa， 15-LOX以n-3二十二碳五烯酸为原料合成epdn - 3dpa。此外，还发现了一种水解酶参与epdn - 3dpa到pd1n - 3dpa的生物合成转化。此外，发现ePDn-3 DPA调节中性粒细胞趋化剂LTB4的形成，其效力与PD1n-3 DPA相同。
PD1n-3 DPA is a specialized pro-resolving lipid mediator that displays potent anti-inflammatory properties and pro-resolving bioactivities. Such naturally occurring compounds are of current interest in biomolecular chemistry and drug discovery. To investigate the involvement of an epoxide intermediate in the biosynthesis of PD1n-3 DPA from n-3 docosapentaenoic acid, the epoxy acid 16(S),17(S)-epoxy-PDn-3 DPA, herein named ePDn-3 DPA, was prepared by stereoselective total synthesis. The synthetic material of ePDn-3 DPA allowed investigations of its role in the biosynthesis of PD1n-3 DPA. The obtained results establish that the biosynthesis of PD1n-3 DPA in neutrophils occurs with ePDn-3 DPA as the intermediate, and that 15-LOX produces ePDn-3 DPA from n-3 docosapentaenoic acid. Furthermore, support for the involvement of a hydrolytic enzyme in the biosynthetic conversion of ePDn-3 DPA to PD1n-3 DPA was found. In addition, ePDn-3 DPA was found to regulate the formation of the potent neutrophil chemoattractant LTB4 with equal potencies to that obtained with PD1n-3 DPA.
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影响因子：
62.1
作者：
Serhan, Charles N.;Petasis, Nicos A.
通讯作者：
Petasis, Nicos A.
影响因子：
5.1
作者：
Aursnes M;Tungen JE;Colas RA;Vlasakov I;Dalli J;Serhan CN;Hansen TV
通讯作者：
Hansen TV
影响因子：
--
作者：
Tjonahen, Eric;Oh, Sungwhan F.;Serhan, Charles N.
通讯作者：
Serhan, Charles N.
影响因子：
3.9
作者：
Wightman, PJ;Santer, R;FitzPatrick, DR
通讯作者：
FitzPatrick, DR
影响因子：
6
作者：
Ramon, Sesquile;Dalli, Jesmond;Serhan, Charles N.
通讯作者：
Serhan, Charles N.