A new total synthesis of the mycotoxin ochratoxin A (OTA) is presented (9% overall yield from commercially available substrates). The key step consists in the condensation reaction between protected L-phenylalanine and 5-chloro-8-hydroxy-3-methyl-1-oxoisochroman-7-carboxylic acid, known as ochratoxin alpha (OTalpha). Using d5-L-phenylalanine, the same strategy could be successfully applied to the first total synthesis of d5-OTA, a molecular tracer for the detection and analytic quantification of the natural mycotoxin in food samples by means of SIDA (stable isotope dilution assay).

A new total synthesis of the mycotoxin ochratoxin A (OTA) is presented, in which it is prepared in 9% overall yield from commercially available Substrates. The key step consists of the condensation reaction between protected L-phenylalanine and 5-chloro-8-hydroxy-3-methyl-1-oxoisochromane-7-carboxylic acid (ochratoxin alpha, OT alpha). The same strategy could be successfully applied to L-d(5)-phenylalanine, leading to the first total synthesis of d(5)-OTA a molecular tracer (or the detection and analytical quantification of the natural mycotoxin in food samples by means of stable isotope dilution assay (SIDA). RI Di Donna, Leonardo/D-5707-2011

A New and Expedient Total Synthesis of Ochratoxin A and d(5)-Ochratoxin A

Gabriele B.;Fazio A.;Di Donna L.;Plastina P.;
2009-01-01

Abstract

A new total synthesis of the mycotoxin ochratoxin A (OTA) is presented (9% overall yield from commercially available substrates). The key step consists in the condensation reaction between protected L-phenylalanine and 5-chloro-8-hydroxy-3-methyl-1-oxoisochroman-7-carboxylic acid, known as ochratoxin alpha (OTalpha). Using d5-L-phenylalanine, the same strategy could be successfully applied to the first total synthesis of d5-OTA, a molecular tracer for the detection and analytic quantification of the natural mycotoxin in food samples by means of SIDA (stable isotope dilution assay).
2009
A new total synthesis of the mycotoxin ochratoxin A (OTA) is presented, in which it is prepared in 9% overall yield from commercially available Substrates. The key step consists of the condensation reaction between protected L-phenylalanine and 5-chloro-8-hydroxy-3-methyl-1-oxoisochromane-7-carboxylic acid (ochratoxin alpha, OT alpha). The same strategy could be successfully applied to L-d(5)-phenylalanine, leading to the first total synthesis of d(5)-OTA a molecular tracer (or the detection and analytical quantification of the natural mycotoxin in food samples by means of stable isotope dilution assay (SIDA). RI Di Donna, Leonardo/D-5707-2011
Natural products; Ochratoxin A; Total synthesis
File in questo prodotto:
Non ci sono file associati a questo prodotto.

I documenti in IRIS sono protetti da copyright e tutti i diritti sono riservati, salvo diversa indicazione.

Utilizza questo identificativo per citare o creare un link a questo documento: https://hdl.handle.net/20.500.11770/138567
 Attenzione

Attenzione! I dati visualizzati non sono stati sottoposti a validazione da parte dell'ateneo

Citazioni
  • ???jsp.display-item.citation.pmc??? ND
  • Scopus 14
  • ???jsp.display-item.citation.isi??? 12
social impact