Solid-phase synthesis of callipeltin D. Stereochemical confirmation of the unnatural amino acid AGDHE.
[structure: see text] The lipopeptide callipeltin D (1) was synthesized using an Fmoc-based solid-phase strategy in seven steps and 35% overall yield. The 1H NMR of synthetic 1 correlated closely with that of the natural product, confirming the configurational assignment of the novel amino acid constituent (2R,3R,4S)-4-amino-7-guanidino-2,3-dihydroxyheptanoic acid.
Cranfill
David C
DC
Department of Chemistry and Cancer Center, Purdue University, 560 Oval Drive, West Lafayette, Indiana 47907-2084, USA.
Morales-Ramos
Angel I
AI
Lipton
Mark A
MA
D000596:Amino Acids / Q000737:chemistry*; D000818:Animals; D047630:Depsipeptides / Q000138:chemical synthesis*; D006146:Guanidines / Q000737:chemistry*; D006538:Heptanoic Acids / Q000737:chemistry*; D015394:Molecular Structure; D011161:Porifera / Q000737:chemistry
C470817:4-amido-7-guanidino-2,3-dihydroxyheptanoic acid; C513051:4-amino-7-guanidino-2,3-dihydroxyheptanoic acid; D000596:Amino Acids; D047630:Depsipeptides; D006146:Guanidines; D006538:Heptanoic Acids; C470816:callipeltin D