Literature

Abstract

A reduced peptide bond analogue of RA-VII, [Tyr-5-Ψ(CH(2)NMe)-Tyr-6]RA-VII (3), was designed and synthesized. The key reduced cycloisodityrosine unit was prepared by reduction of the cycloisodityrosine derived from natural RA-VII, followed by connection with the tetrapeptide segment to afford a hexapeptide. Subsequent macrocyclization of the hexapeptide with FDPP under dilute conditions gave 3. Analogue 3 showed cytotoxic activity against P-388 cells, but its activity was much weaker than that of parent peptide RA-VII.

DOI： 10.1016/j.bmcl.2012.02.093

Synthesis of [Tyr-5-Ψ(CH2NMe)-Tyr-6]RA-VII, a reduced peptide bond analogue of RA-VII, an antitumor bicyclic hexapeptide

Bioorganic & Medicinal Chemistry Letters 2012.0

Design and synthesis of a bis(cycloisodityrosine) analogue of RA-VII, an antitumor bicyclic hexapeptide

Bioorganic & Medicinal Chemistry Letters 2008.0

Aza-cycloisodityrosine analogue of RA-VII, an antitumor bicyclic hexapeptide

Bioorganic & Medicinal Chemistry Letters 2013.0

Per-N-methylated analogues of an antitumor bicyclic hexapeptide RA-VII

Bioorganic & Medicinal Chemistry 2011.0

Preparation and antitumor activity of [N-alkyl-Ala2]RA-VII, antitumor cyclic hexapeptide

Bioorganic & Medicinal Chemistry Letters 1994.0

Isolation, structural elucidation, and synthesis of RA-XVII, a novel bicyclic hexapeptide from Rubia cordifolia, and the effect of side chain at residue 1 upon the conformation and cytotoxic activity