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Synthesis of the N-terminal lipohexapeptide of human G(alpha o)-protein and fluorescent-labeled analogues for biological studies

MPG-Autoren
http://pubman.mpdl.mpg.de/cone/persons/resource/persons98707

Kuhlmann,  Jürgen
Sonstige Wissenschaftliche Organisationseinheiten, Max Planck Institute of Molecular Physiology, Max Planck Society;

http://pubman.mpdl.mpg.de/cone/persons/resource/persons98735

Waldmann,  Herbert
Abt. IV: Chemische Biologie, Max Planck Institute of Molecular Physiology, Max Planck Society;

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Zitation

Cotte, A., Bader, B., Kuhlmann, J., & Waldmann, H. (1999). Synthesis of the N-terminal lipohexapeptide of human G(alpha o)-protein and fluorescent-labeled analogues for biological studies. CHEMISTRY-A EUROPEAN JOURNAL, 5(3), 922-936. doi:10.1002/(SICI)1521-3765(19990301)5:3<922:AID-CHEM922>3.3.CO;2-F.


Zitierlink: http://hdl.handle.net/11858/00-001M-0000-0014-711C-F
Zusammenfassung
For the study of biological signal transduction via heterotrimeric N-myristoylated and S-palmitoylated G proteins, useful reagents may be lipidated peptides that contain the lipid groups and amino acid sequences of their parent lipoproteins. The synthesis of S-palmitoylated peptides like Myr-Gly-Cys(Pal)-Thr-Leu-Ser-Ala-OH (I), which represents the characteristic N-terminus of the alpha-subunit of human G(alpha O) protein, is complicated by the pronounced base- lability of the thioester. Lipidated G-protein peptide I and various fluorescent-labeled analogues thereof were built up efficiently by employing either the Pd-0-mediated removal of the allyl ester or the butyryl choline esterase-catalysed cleavage of the choline ester as key step. The removal of both blocking functions proceeds under very mild conditions and without undesired side reactions. In the cases studied the allyl ester proved to be superior to the enzyme-labile choline ester. The fluorescent-labeled lipopeptides were subjected to microinjection experiments in NIH-3T3 cells, which revealed that the compounds meet basic requirements for application in biology.