Key analogues of the tetrapeptide subunit of RA-VII and deoxybouvardin.
The synthesis and evaluation of the analogues 3 and 4 of deoxybouvardin (1) and RA-VII (2), which contain modifications in the tetrapeptide subunit, are described. Unlike the natural products and similar to our prior disclosure, the agents 3 and 4, which substitute (Gly)4 and (Gly)3 for the D-Ala-Ala-NMe-Tyr(OMe)-Ala tetrapeptide subunit, exist in single rigid conformations in which the central cycloisodityrosine amide adopts its preferred trans stereochemistry and both were found to be biologically inactive.
Boger
D L
DL
Department of Chemistry, Scripps Research Institute, La Jolla, CA 92037, USA.
Zhou
J
J
D000818:Animals; D000972:Antineoplastic Agents, Phytogenic / Q000737:chemistry*; D018360:Crystallography, X-Ray; D008958:Models, Molecular; D010456:Peptides, Cyclic / Q000737:chemistry*; D011487:Protein Conformation; D014407:Tumor Cells, Cultured
D000972:Antineoplastic Agents, Phytogenic; D010456:Peptides, Cyclic; C043547:RA V; C043548:RA VII