Journal
MONATSHEFTE FUR CHEMIE
Volume 140, Issue 1, Pages 121-127Publisher
SPRINGER WIEN
DOI: 10.1007/s00706-008-0052-z
Keywords
Natural products; Hirsutide; Peptides; Cyclizations; Total synthesis; Biological activity
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The present investigation deals with the synthesis of a N-methylated cyclotetrapeptide, hirsutide (2), by coupling of the dipeptide units Boc-L-phenylalanyl-L-N-methylphenylalanine-OH and L-valyl-L-N-methylphenylalanine-OMe followed by cyclization of the linear tetrapeptide fragment. The chemical structure was established on the basis of analytical as well as spectroscopic data. The newly synthesized cyclic peptide was subjected to pharmacological screening and found to be highly potent against the gram-negative bacteria Pseudomonas aeruginosa and Klebsiella pneumoniae at 6 mu g cm(-3). In addition, potent antihelmintic activity against the earthworms Megascoplex konkanensis and Pontoscotex corethruses at 1 and 2 mg cm(-3), and potent cytotoxic activity against Dalton's lymphoma ascites and Ehrlich's ascites carcinoma cell lines with IC50 values of 14 and 22 mu M were also observed. Studies revealed that the pentafluorophenyl ester method employing a catalytic amount of N-methylmorpholine proved to be better for cyclization of the linear tetrapeptide unit.
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