Synthesis of borondipyrromethene (BODIPY)-labeled sphingosine derivatives by cross-metathesis reaction.
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.
Peters
Carsten
C
Novartis Institutes for BioMedical Research, Brunnerstrasse 59, A-1235 Vienna, Austria.
Billich
Andreas
A
Ghobrial
Michael
M
Högenauer
Klemens
K
Ullrich
Thomas
T
Nussbaumer
Peter
P
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
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