Solid-phase total synthesis and structure proof of callipeltin B.
The cytotoxic, cyclic heptadepsipeptide, natural product callipeltin B was synthesized on a solid-phase support in 15% overall yield. Comparison of the 1H NMR spectra of three synthetic isomers with those of callipeltin B confirmed the configurational reassignment of its threonine residues as d-allothreonine and the assignment of the configuration of its beta-methoxytyrosine residue as (2R,3R).
Krishnamoorthy
Ravi
R
Department of Chemistry and Cancer Center, Purdue University, 560 Oval Drive, West Lafayette, Indiana 47907-2084, USA.
Vazquez-Serrano
Leslie D
LD
Turk
Jeffrey A
JA
Kowalski
Jennifer A
JA
Benson
Alan G
AG
Breaux
Nneka T
NT
Lipton
Mark A
MA
D000818:Animals; D047630:Depsipeptides / Q000138:chemical synthesis* / Q000737:chemistry / Q000302:isolation & purification; D010456:Peptides, Cyclic / Q000138:chemical synthesis* / Q000737:chemistry / Q000302:isolation & purification; D011161:Porifera / Q000737:chemistry; D011487:Protein Conformation
D047630:Depsipeptides; D010456:Peptides, Cyclic; C516600:callipeltin B