Synthesis of N alpha-Fmoc protected derivatives of S-(2,3-dihydroxypropyl)-cysteine and their application in peptide synthesis.
Acylated derivatives of S-(2,3-dihydroxypropyl)-cysteine (S-glycerylcysteine) form the N-terminus of structural and functional proteins of bacterial origin. Synthetic lipopeptides containing tripalmitoyl-S-glycerylcysteine are derived from bacterial lipoprotein and constitute potent immunoadjuvants activating both B-lymphocytes and macrophages. There is increasingly interest in conjugates consisting of tripalmitoyl-S-glycerylcysteine linked to appropriate viral and bacterial antigens, because of their capability of inducing antigen specific antibodies and T-helper and T-killer cell specific immune responses. A new convenient synthetic pathway for the preparation of these tripalmitoyl-S-glycerylcysteinyl peptides is described. The use of N alpha-Fmoc-protected S-(2,3-dihydroxypropyl)-cysteine and its O,O'-bis acylated derivatives for the synthesis of triacyl-S-glycerylcysteinyl, O,O'-bis-acyl-S-glycerylcysteinyl and S-glycerylcysteinyl peptides of high diastereomeric purity by solid phase peptide synthesis or synthesis in solution is demonstrated.
Metzger
J W
JW
Institute of Organic Chemistry, University of Tübingen, FRG.
Wiesmüller
K H
KH
Jung
G
G
D000595:Amino Acid Sequence; D000596:Amino Acids / Q000138:chemical synthesis / Q000737:chemistry; D001426:Bacterial Proteins / Q000737:chemistry; D003545:Cysteine / Q000031:analogs & derivatives* / Q000138:chemical synthesis / Q000737:chemistry; D005449:Fluorenes / Q000138:chemical synthesis / Q000737:chemistry; D008074:Lipoproteins / Q000138:chemical synthesis / Q000737:chemistry; D009682:Magnetic Resonance Spectroscopy; D013058:Mass Spectrometry; D008969:Molecular Sequence Data; D015394:Molecular Structure; D010455:Peptides / Q000138:chemical synthesis* / Q000737:chemistry
D000596:Amino Acids; D001426:Bacterial Proteins; D005449:Fluorenes; D008074:Lipoproteins; C016456:N(alpha)-fluorenylmethyloxycarbonylamino acids; D010455:Peptides; C031164:glycerylcysteine; D003545:Cysteine