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Synthesis of borondipyrromethene (BODIPY)-labeled sphingosine derivatives by cross-metathesis reaction.

Peters, Carsten and Billich, Andreas and Ghobrial, Micha and Hoegenauer, Klemens and Ullrich, Thomas and Nussbaumer, Peter (2007) Synthesis of borondipyrromethene (BODIPY)-labeled sphingosine derivatives by cross-metathesis reaction. The Journal of Organic Chemistry, 72 (5). pp. 1842-1845. ISSN 0022-3263

Abstract

A new efficient and flexible synthesis of fluorescently labeled sphingosine derivatives from commercially available Garner aldehyde (8) is described. For this, appropriate alkenylated borondipyrromethene (BODIPY) dyes were synthesized and used for the first time in a cross-metathesis reaction, the key step of the approach. The labeled sphingosines with appropriate chain length were accepted as substrates by sphingosine kinases (SPHKs), yielding the corresponding phosphorylated products. One of these derivatives (11d) was identified as the first reported selective substrate for SPHK-1.

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Date Deposited: 14 Dec 2009 13:58
Last Modified: 31 Jan 2013 01:14
URI: https://oak.novartis.com/id/eprint/541

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