title: Synthesis of borondipyrromethene (BODIPY)-labeled sphingosine derivatives by cross-metathesis reaction.
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.
authors.affiliation: Novartis Institutes for BioMedical Research, Brunnerstrasse 59, A-1235 Vienna, Austria.
authors.forename: Carsten
authors.initials: C
authors.lastname: Peters
authors.forename: Andreas
authors.initials: A
authors.lastname: Billich
authors.forename: Michael
authors.initials: M
authors.lastname: Ghobrial
authors.forename: Klemens
authors.initials: K
authors.lastname: Högenauer
authors.forename: Thomas
authors.initials: T
authors.lastname: Ullrich
authors.forename: Peter
authors.initials: P
authors.lastname: Nussbaumer
mesh_terms: D000447:Aldehydes / Q000737:chemistry; D001896:Boron Compounds / Q000138:chemical synthesis*; D002851:Chromatography, High Pressure Liquid; D005456:Fluorescent Dyes / Q000138:chemical synthesis* / Q000737:chemistry; D007202:Indicators and Reagents; D007700:Kinetics; D009682:Magnetic Resonance Spectroscopy; D010766:Phosphorylation; D017853:Phosphotransferases (Alcohol Group Acceptor) / Q000378:metabolism; D021241:Spectrometry, Mass, Electrospray Ionization; D013110:Sphingosine / Q000031:analogs & derivatives* / Q000138:chemical synthesis* / Q000378:metabolism; D000099157:Sphingosine Kinase
chemical_list: D000447:Aldehydes; D001896:Boron Compounds; D005456:Fluorescent Dyes; D007202:Indicators and Reagents; D017853:Phosphotransferases (Alcohol Group Acceptor); D013110:Sphingosine; D000099157:Sphingosine Kinase; C095489:4,4-difluoro-4-bora-3a,4a-diaza-s-indacene