Synthesis of thiol-functionalized N-acetylmuramyl peptide congeners suitable for their conjugation to target molecules.
N-Acetylmuramyl-dipeptide and tripeptide derivatives containing at the C-terminus a masked thiol function, i.e. the S-tert-butylthiocysteamine residue, were synthesized via direct condensation of N-acetylmuramic acid with the peptide moiety using the dicyclohexylcarbodiimide/N-hydroxysuccinimide procedure. Reduction with tributylphosphine in aqueous organic media generates the free thiol function for a selective conjugation of these immunomodulants with target molecules via unsymmetrical disulfide bridging with a second thiol group by the sulfenohydrazide procedure or via thio-ether linkage by the addition to maleimido--or aziridine-derivatives.
Moroder
L
L
Max-Planck-Institut für Biochemie, Abteilung Peptidchemie, Martinsried München.
Gobbo
M
M
Becker
G
G
Wünsch
E
E
D000119:Acetylmuramyl-Alanyl-Isoglutamine / Q000031:analogs & derivatives* / Q000138:chemical synthesis; D055598:Chemical Phenomena; D002621:Chemistry; D002851:Chromatography, High Pressure Liquid; D009682:Magnetic Resonance Spectroscopy; D010084:Oxidation-Reduction; D010455:Peptides / Q000138:chemical synthesis*
D010455:Peptides; D000119:Acetylmuramyl-Alanyl-Isoglutamine