Synthesis of analogues of ochratoxin A

Abstract

Four analogues of ochratoxin A (OTA) differing for the aminoacidic moiety were synthesised using ochratoxin α (OTα) as the starting material. The condensation reaction between protected amino acids and OTα, carried out in the presence of 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide hydrochloride (EDC • HCl) and N-hydroxybenzotriazole (HOBt) as coupling agents, followed by deprotection and PTLC purification afforded OTA alanine, leucine, serine and tryptophane analogues in satisfactory yields (33–47%, based on OTα).

Keywords:

• ochratoxin A
• OTA
• ochratoxin analogues
• synthesis
• diastereomeric analogues

Acknowledgement

Mohamed Attya gratefully acknowledges Calabria QUASIORA laboratory for his post-doctoral grant.