Validation of a solid-phase-bound steroid scaffold for the synthesis of novel cyclic peptidosteroids.
The current article reports on the synthesis of a new type of cyclic peptidosteroid, in which a bile-acid-based scaffold was used for the conformational restriction of a loop-like peptide. Convergent coupling of two tetrapeptides to the non-peptidic steroidal entity was carried out once in the classical C-to-N and once in the non-classical N-to-C direction. Peptide backbone cyclisation was then carried out, giving rise to a ring size equivalent to approximately 12 amino acids. This type of construct will be used in the development of a peptide vaccine against measles.
Bodé
Catherine A
CA
Laboratory for Organic and Biomimetic Chemistry, Department of Organic Chemistry, Ghent University, B-9000 Gent, Belgium.
Muller
Claude P
CP
Madder
Annemieke
A
D000595:Amino Acid Sequence; D001647:Bile Acids and Salts / Q000737:chemistry; D006801:Humans; D015394:Molecular Structure; D010456:Peptides, Cyclic / Q000138:chemical synthesis / Q000737:chemistry; D015203:Reproducibility of Results; D013256:Steroids / Q000138:chemical synthesis / Q000737:chemistry; D014612:Vaccines / Q000138:chemical synthesis
D001647:Bile Acids and Salts; D010456:Peptides, Cyclic; D013256:Steroids; D014612:Vaccines