title: Synthesis of the amino acid conjugates of epi-jasmonic acid.
abstract: The TES ether of the C6-hydroxy derivative of naturally occurring epi-jasmonic acid (epi-JA) was designed as epimerization-free equivalent of epi-JA. The TES ether was synthesized from (1R,4S)-4-hydroxycyclopent-2-enyl acetate in 13 steps. The acid part of the ether was activated with ClCO2Bui and subjected to condensation with L-amino acid at room temperature for 48 h. The TES group in the condensation product was removed in HCO2H (0°C, 30 min) and the resulting hydroxyl group was oxidized with Jones reagent (acetone, 0°C, 30 min) to furnish the amino acid conjugate of epi-JA. The amino acids examined are L-isoleucine, L-leucine, L-alanine, L-valine, and D-allo-isoleucine, which afforded the conjugates in 48-68% yields with 89-96% diastereomeric purity over the trans isomers. Similarly, the possible three stereoisomers of epi-JA were condensed with L-isoleucine successfully, producing the corresponding stereoisomers in good yields.
authors.affiliation: Department of Biomolecular Engineering, Tokyo Institute of Technology, B52, Nagatsuta-cho 4259, Midori-ku, Yokohama, 226-8501, Japan.
authors.forename: N
authors.initials: N
authors.lastname: Ogawa
authors.forename: Y
authors.initials: Y
authors.lastname: Kobayashi
mesh_terms: D000409:Alanine / Q000737:chemistry; D003517:Cyclopentanes / Q000138:chemical synthesis* / Q000737:chemistry; D007532:Isoleucine / Q000031:analogs & derivatives / Q000138:chemical synthesis*; D015394:Molecular Structure; D054883:Oxylipins / Q000138:chemical synthesis* / Q000737:chemistry; D010944:Plants / Q000737:chemistry; D013237:Stereoisomerism; D014633:Valine / Q000737:chemistry
chemical_list: D003517:Cyclopentanes; D054883:Oxylipins; D007532:Isoleucine; C011006:jasmonic acid; D014633:Valine; D000409:Alanine