Literature DB >> 5131015

Oximes, nitriles and 2-hydroxynitriles as precursors in the biosynthesis of cyanogenic glucosides.

B A Tapper, G W Butler.   

Abstract

The biosynthesis of the cyanogenic glucosides, linamarin and prunasin, was investigated in linen-flax, peach and cherry-laurel shoots. It was shown that related 2-oximino acids, aldoximes, nitriles and 2-hydroxynitriles were generally good precursors of the aglycone moiety. Studies with double-labelled compounds confirmed the retention of the oximino nitrogen atom from 2-oximinoisovaleric acid and isobutyraldoxime in the biosynthesis of linamarin. A general pathway from amino acids to cyanogenic glucosides involving N-hydroxyamino acids, aldoximes, nitriles and 2-hydroxynitriles is proposed.

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Year:  1971        PMID： 5131015      PMCID： PMC1177282          DOI： 10.1042/bj1240935

Source DB:  PubMed          Journal:  Biochem J        ISSN： 0264-6021            Impact factor:   3.857


  8 in total

1.  BIOSYNTHESIS OF THE CYANOGENIC GLUCOSIDES LINAMARIN AND LOTAUSTRALIN. I. LABELING STUDIES IN VIVO WITH LINUM USITATISSIMUM.

Authors:  G W BUTLER; E E CONN
Journal:  J Biol Chem       Date:  1964-06       Impact factor: 5.157

2.  [MASSIAS M: (BIOGENESIS OF THE CYANOGENETIC GLUCOSIDE IN PRUNUS LAUROCERASUS)].

Authors:  C MENTZER; J FAVRE-BONVIN
Journal:  Bull Soc Chim Biol (Paris)       Date:  1963-08-31

3.  Conversion of nitriles and alpha-hydroxynitriles to cyanogenic glucosides in flax seedlings and cherry laurel leaves.

Authors:  K Hahlbrock; B A Tapper; G W Butler; E E Conn
Journal:  Arch Biochem Biophys       Date:  1968-06       Impact factor: 4.013

4.  The biosynthesis of cyanogenic glycosides in higher plants. I. Purification and properties of a uridine diphosphate-glucose-ketone cyanohydrin beta-glucosyltransferase from Linum usitatissimum L.

Authors:  K Hahlbrock; E E Conn
Journal:  J Biol Chem       Date:  1970-03-10       Impact factor: 5.157

5.  Separation and estimation of amino acids in crude plant extracts by thin-layer electrophoresis and chromatography.

Authors:  R L Bieleski; N A Turner
Journal:  Anal Biochem       Date:  1966-11       Impact factor: 3.365

6.  The metabolism of aromatic compounds in higher plants. VII. The origin of the nitrile nitrogen atom of dhurrin (beta-D-glucopyranosyloxy-L-p-hydroxymandelonitrile).

Authors:  E G Uribe; E E Conn
Journal:  J Biol Chem       Date:  1966-01-10       Impact factor: 5.157

7.  Incorporation of C14 into p-hydroxymandelonitrile-beta-glucose and other phenolic substances in sorghum seedlings.

Authors:  J E GANDER
Journal:  J Biol Chem       Date:  1962-10       Impact factor: 5.157

8.  Conversion of alpha-keto-isovaleric acid oxime and isobutyraldoxime to linamarin in flax seedlings.

Authors:  B A Tapper; E E Conn; G W Butler
Journal:  Arch Biochem Biophys       Date:  1967-03       Impact factor: 4.013
  8 in total

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