Synthesis of the celogentin C right-hand ring.
[reaction: see text] Synthesis of the cyclic tetrapeptide comprising the right-hand ring of celogentin C, a potent inhibitor of tubulin polymerization, has been accomplished. A mild oxidative coupling reaction permitted construction of the indole-imidazole linkage via a convergent union of two fully functionalized dipeptides. A high-yielding macrolactamization and subsequent deprotection of the N-terminus furnished the target compound.
He
Liwen
L
Department of Chemistry and Biochemistry, Brigham Young University, Provo, Utah 84602, USA.
Yang
Liping
L
Castle
Steven L
SL
D034762:Celosia / Q000737:chemistry; D015394:Molecular Structure; D010456:Peptides, Cyclic / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology; D050257:Tubulin Modulators / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology
D010456:Peptides, Cyclic; D050257:Tubulin Modulators; C445725:celogentin C