Synthesis of Borondipyrromethene (BODIPY)-Labeled Sphingosine Derivatives by Cross-metathesis Reaction

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• 作者：Carsten Peters ; Andreas Billich ; Michael Ghobrial ; Klemens Hö ; genauer ; Thomas Ullrich ; Peter Nussbaumer
• 刊名：Journal of Organic Chemistry
• 出版年：2007
• 出版时间：March 2, 2007
• 年：2007
• 卷：72
• 期：5
• 页码：1842 - 1845
• 全文大小：77K
• 年卷期：v.72,no.5(March 2, 2007)
• ISSN：1520-6904

文摘

A new efficient and flexible synthesis of fluorescently labeledsphingosine derivatives from commercially available Garneraldehyde (8) is described. For this, appropriate alkenylatedborondipyrromethene (BODIPY) dyes were synthesized andused for the first time in a cross-metathesis reaction, the keystep of the approach. The labeled sphingosines with appropriate chain length were accepted as substrates bysphingosine kinases (SPHKs), yielding the correspondingphosphorylated products. One of these derivatives (11d) wasidentified as the first reported selective substrate forSPHK-1.