Preparative-scale synthesis and physicochemical properties of cysteine and glutathione conjugates of chloroacetamides

I. Jablonkai, Ferenc Dutka

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5 Citations (Scopus)

Abstract

The preparative-scale syntheses of cysteine and glutathione (GSH) conjugates (2,3) of the chloroacetanilide herbicide acetochlor (1a) and its plant degradation products (1b,c) were accomplished in high yield and in excellent purity by the reaction of chloroacetamides with stoichiometric GSH or cysteine in liquid ammonia in the presence of sodium amide. Cysteine conjugates of metabolites 1b,c without an N-alkoxyalkyl side chain could easily be prepared in alcoholic solutions of cysteine hydrochloride and sodium ethoxide by reactions with chloroacetamides. The physicochemical properties and 1H NMR data of conjugates are also described.

Original languageEnglish
Pages (from-to)506-508
Number of pages3
JournalJournal of Agricultural and Food Chemistry
Volume40
Issue number3
Publication statusPublished - 1992

Fingerprint

Glutathione
Cysteine
cysteine
glutathione
physicochemical properties
synthesis
chloroacetanilide herbicides
sodium
acetochlor
alcohol abuse
Metabolites
amides
Ammonia
Amides
purity
ammonia
Sodium
Nuclear magnetic resonance
metabolites
Degradation

ASJC Scopus subject areas

  • Agricultural and Biological Sciences (miscellaneous)
  • Food Science
  • Chemistry (miscellaneous)

Cite this

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AU - Jablonkai, I.

AU - Dutka, Ferenc

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N2 - The preparative-scale syntheses of cysteine and glutathione (GSH) conjugates (2,3) of the chloroacetanilide herbicide acetochlor (1a) and its plant degradation products (1b,c) were accomplished in high yield and in excellent purity by the reaction of chloroacetamides with stoichiometric GSH or cysteine in liquid ammonia in the presence of sodium amide. Cysteine conjugates of metabolites 1b,c without an N-alkoxyalkyl side chain could easily be prepared in alcoholic solutions of cysteine hydrochloride and sodium ethoxide by reactions with chloroacetamides. The physicochemical properties and 1H NMR data of conjugates are also described.

AB - The preparative-scale syntheses of cysteine and glutathione (GSH) conjugates (2,3) of the chloroacetanilide herbicide acetochlor (1a) and its plant degradation products (1b,c) were accomplished in high yield and in excellent purity by the reaction of chloroacetamides with stoichiometric GSH or cysteine in liquid ammonia in the presence of sodium amide. Cysteine conjugates of metabolites 1b,c without an N-alkoxyalkyl side chain could easily be prepared in alcoholic solutions of cysteine hydrochloride and sodium ethoxide by reactions with chloroacetamides. The physicochemical properties and 1H NMR data of conjugates are also described.

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