CYCLIC-PEPTIDES .19. SYNTHESIS, CONFORMATION, AND BIOLOGICAL-ACTIVITY OF CYCLO(-PRO-VAL-PRO-VAL-) WITH L-L-L-L AND L-D-L-D SEQUENCES

  • 1 January 1985
    • journal article
    • research article
    • Vol. 25  (5) , 475-480
Abstract
Cyclo(-L-Pro-L-Val-L-Pro-L-Val-) (1L) and cyclo(-L-Pro-D-Val-L-Pro-D-Val-) (1D) were synthesized by the conventional method for peptide synthesis. Conformations of 1L and 1D in solution were studied. Compound 1L has a cis-trans-cis-trans backbone conformation with C2 symmetry in CDCl3. This conformation is slightly different from that in crystalline state and in DMSO[dimethylsulfoxide]-d6 solution. Compound 1D has a cis-trans-cis-tans conformation in DMSO-d6 and in all-trans conformation in trifluoroethanol-d3. Compound 1L retarded stem-growth of rice seedlings and, in contrast, compound 1D promoted root-growth of rice seedlings.