磷脂酰肌醇-3-亚甲基磷酸酯的合成与分子识别
Synthesis and molecular recognition of phosphatidylinositol-3-methylenephosphate.
作者信息
Gajewiak Joanna, Xu Yong, Lee Stephanie A, Kutateladze Tatiana G, Prestwich Glenn D
机构信息
Department of Medicinal Chemistry, The University of Utah, Salt Lake City, 84108-1257, USA.
出版信息
Org Lett. 2006 Jun 22;8(13):2811-3. doi: 10.1021/ol060903i.
Abstract
[reaction: see text] Phosphatidylinositol-3-phosphate (PtdIns(3)P) is a spatial regulator of vesicular trafficking and other vital cellular processes. We describe the asymmetric total synthesis of a metabolically stabilized analogue, phosphatidylinositol-3-methylenephosphate (PtdIns(3)MP) from a differentially protected myo-inositol. NMR studies of PtdIns(3)MP bound to the (15)N-labeled FYVE domain showed significant (1)H and (15)N chemical shift changes relative to the unliganded protein.
摘要
[反应：见正文] 磷脂酰肌醇-3-磷酸（PtdIns(3)P）是囊泡运输及其他重要细胞过程的空间调节因子。我们描述了一种代谢稳定类似物磷脂酰肌醇-3-亚甲基磷酸（PtdIns(3)MP）从差异保护的肌醇的不对称全合成。对与(15)N标记的FYVE结构域结合的PtdIns(3)MP的核磁共振研究表明，相对于未结合配体的蛋白质，其(1)H和(15)N化学位移有显著变化。
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2
Acyclic nucleoside phosphonates: a key class of antiviral drugs.
Nat Rev Drug Discov. 2005 Nov;4(11):928-40. doi: 10.1038/nrd1877.
3
Targeting of the FYVE domain to endosomal membranes is regulated by a histidine switch.
Proc Natl Acad Sci U S A. 2005 Sep 13;102(37):13052-7. doi: 10.1073/pnas.0503900102. Epub 2005 Sep 2.
4
Phosphonomethylphosphorylmethyl(oxy)-analogues of geranylgeranyl diphosphate as stable and selective geranylgeranyl protein transferase inhibitors.
Farmaco. 2004 Nov;59(11):887-92. doi: 10.1016/j.farmac.2004.08.002.
5
Phosphoinositide signaling; from affinity probes to pharmaceutical targets.
Chem Biol. 2004 May;11(5):619-37. doi: 10.1016/j.chembiol.2004.03.025.
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J Cell Biol. 2003 Sep 15;162(6):971-9. doi: 10.1083/jcb.200303018.
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Myotubularins, a large disease-associated family of cooperating catalytically active and inactive phosphoinositides phosphatases.
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