Elsevier

Analytical Biochemistry

Volume 38, Issue 1, November 1970, Pages 46-55
Analytical Biochemistry

Enzymic synthesis of l-ascorbic acid from synthetic and biological d-glucurono-1,4-lactone conjugates

https://doi.org/10.1016/0003-2697(70)90154-5Get rights and content

Abstract

d-Glucofuranosiduronolactone conjugates, namely, semicarbazone, oxime, cyanohydrin, and thioacetal of d-glucurono-1,4-lactone, were converted to l-ascorbic acid by an enzyme system present in rat, goat, or rabbit liver microsomes. Guinea pig liver microsomes were ineffective. Neither methyl-d-glucofuranosiduronolactone nor any glucopyranosiduronic acid conjugates examined were converted into l-ascorbic acid. Methods of preparation and properties of d-glucurono-1,4-lactone semicarbazone and d-glucurono-1,4-lactone oxime have been described and a tentative mechanism of enzymic reduction of the conjugates into l-gulono-1,4-lactone has been suggested.

A conjugate of d-glucurono-1,4-lactone and imidazole, which is a substrate for the microsomal enzyme leading to synthesis of l-ascorbic acid, has been identified in the urine of rat treated with chloretone, barbital, and 1,2-benzanthracene. It has been indicated that the enhanced synthesis of l-ascorbic acid after administration of various drugs and toxic chemical compounds is due to the induced formation of this endogenous substrate.

References (22)

  • F. Lipmann et al.

    J. Biol. Chem

    (1945)
  • H.E. Longenecker et al.

    J. Biol. Chem

    (1940)
  • J.J. Burns et al.

    J. Biol. Chem

    (1957)
  • F. Eisenberg et al.

    J. Biol. Chem

    (1956)
  • W.H. Fishman et al.

    J. Biol. Chem

    (1955)
  • I.B. Chatterjee et al.

    Arch. Biochem. Biophys

    (1965)
  • I.B. Chatterjee et al.

    Science

    (1957)
  • I.B. Chatterjee et al.

    Biochem. J

    (1960)
  • I.B. Chatterjee et al.

    Biochem. J

    (1958)
  • I.B. Chatterjee et al.

    Biochem. J

    (1960)
  • S. Dutta Gupta et al.

    Naturwissenschaften

    (1967)
  • Cited by (8)

    • Is L-gulonolactone-oxidase the only enzyme missing in animals subject to scurvy?

      1976, Biochemical and Biophysical Research Communications
    • Incapability of l-ascorbic acid synthesis by insects

      1972, Archives of Biochemistry and Biophysics
    View all citing articles on Scopus
    View full text