Biosynthesis of Mustard Oil Glucosides: Sodium Phenylacetothiohydroximate and Desulfobenzylglucosinolate, Precursors of Benzylglucosinolate in Tropaeolum majus.

The biosynthesis of the mustard oil glucoside, benzylglucosinolate, was studied in Tropaeolum majus L. A number of labeled compounds were administered to plant shoots and the incorporation of tracer into benzylglucosinolate, isolated as the crystalline tetramethyl-ammonium salt, was measured. In order of decreasing efficiency of conversion into benzyl-glucosinolate the compounds fed were S-(beta-d-glucopyranosyl)phenylacetothiohydroximic acid (desulfobenzylglucosinolate), sodium phenylacetothiohydroximate, dl-phenylalanine, d-glucose, and sodium-d-1-glucopyranosyl mercaptide (1-thioglucose). The results are consistent with the hypothesis that the thioglucosyl group of benzylglucosinolate is derived by glucosylation of phenylacetothiohydroximate and not from 1-thioglucose. The results also suggest that benzylglucosinolate is formed by sulfation of desulfobenzylglucosinolate as the final step in its biosynthesis.A method for the isolation of a number of glucosinolates (mustard oil glucosides) is described which utilizes anion exchange chromatography on diethylaminoethyl (DEAE) cellulose. Potassium allylglucosinolate, tetramethylammonium benzylglucosinolate, potassium 2-hydroxy-2-phenylethylglucosinolate and potassium 2-phenylethylglucosinolate were obtained on recrystallization of the glucosinolate fraction eluted from the column.

[1]  M. Chisholm,et al.  Sources of sulfur in the thioglucosides of various higher plants. , 1968, Canadian journal of biochemistry.

[2]  M. Matsuo.  Biosynthesis of sinigrin. V. On the origin of thioglucoside moiety of sinigrin. , 1968, Chemical & pharmaceutical bulletin.

[3]  T. Gessner,et al.  Metabolism of thiols. S-Glucosylation. , 1968, The Journal of biological chemistry.

[4]  H. Kindl.  Biosynthesis of mustard oil glucosides: N-Hydroxyphenylalanine, a precursor of glucotropaeolin and a substrate for the enzymatic and nonenzymatic formation of phenylacetaldehyde oxime , 1968 .

[5]  G. Howard,et al.  Glucosyl transfer by beta-thioglucosidase☆ , 1968 .

[6]  E. W. Underhill.  Biosynthesis of Mustard Oil Glucosides , 1967 .

[7]  G. W. Butler,et al.  Conversion of oximes to mustard oil glucosides (Glucosinolates) , 1967 .

[8]  E. W. Underhill.  Biosynthesis of mustard oil glucosides: conversion of phenylacetaldehyde oxime and 3-phenylpropionaldehyde oxime to glucotropaeolin and gluconasturtiin. , 1967, European journal of biochemistry.

[9]  K. Nagata,et al.  Studies on Thiohydroxamic Acids and Their Metal Chelates. III. Syntheses of Some Thiohydroxamic Acid Derivatives and Their Structures , 1966 .

[10]  D. Meakin.  Studies of mustard oil glucosides , 1965 .

[11]  M. Benn.  A NEW MUSTARD OIL GLUCOSIDE SYNTHESIS: THE SYNTHESIS OF GLUCOTROPAEOLIN , 1963 .

[12]  E. W. Underhill,et al.  Biosynthesis of mustard oil glucosides. I. Administration of C14-labelled compounds to horseradish, nasturtium, and watercress. , 1962, Canadian journal of biochemistry and physiology.

[13]  George A. Bray,et al.  A simple efficient liquid scintillator for counting aqueous solutions in a liquid scintillation counter , 1960 .

[14]  M. Ettlinger,et al.  FIRST SYNTHESIS OF A MUSTARD OIL GLUCOSIDE; THE ENZYMATIC LOSSEN REARRANGEMENT , 1957 .

[15]  B. D. Davis.  Intermediates in amino acid biosynthesis. , 1955, Advances in enzymology and related subjects of biochemistry.