Synthesis of the unnatural amino acid AGDHE, a constituent of the cyclic depsipeptides callipeltins A and D.
[reaction: see text] The novel amino acid residue (2R,3R,4S)-4-amido-7-guanidino-2,3-dihydroxyheptanoic acid (AGDHE, 3), a constituent of the cyclic depsipeptides callipeltins A and D, and its (2S,3S,4S) diastereomer were synthesized from a protected L-ornithine derivative in 13 steps (15% overall yield), and its configurational assignment was reexamined by (1)H NMR.
Thoen
Jason C
JC
Department of Chemistry, Purdue University, West Lafayette, Indiana 47907-1393, USA.
Morales-Ramos
Angel I
AI
Lipton
Mark A
MA
D000596:Amino Acids / Q000138:chemical synthesis* / Q000737:chemistry; D000818:Animals; D047630:Depsipeptides; D006146:Guanidines / Q000737:chemistry*; D006538:Heptanoic Acids / Q000737:chemistry*; D009682:Magnetic Resonance Spectroscopy; D015394:Molecular Structure; D010456:Peptides, Cyclic / Q000737:chemistry*; D011161:Porifera / Q000737:chemistry; D013237:Stereoisomerism
C470817:4-amido-7-guanidino-2,3-dihydroxyheptanoic acid; D000596:Amino Acids; D047630:Depsipeptides; D006146:Guanidines; D006538:Heptanoic Acids; D010456:Peptides, Cyclic; C418139:callipeltin A; C470816:callipeltin D