Elsevier

Carbohydrate Research

Volume 189, 15 June 1989, Pages 261-272
Carbohydrate Research

The acetylation of O-3 of galacturonic acid in the rhamnose-rich portion of pectins

https://doi.org/10.1016/0008-6215(89)84102-3Get rights and content

Abstract

Treatment of cell walls isolated from carrot, cotton, tobacco, and tomato with anhydrous hydrogen fluoride (HF) at −23° generated a high yield of disaccharides of galacturonic acid and rhamnose from the backbone of the rhamnose-rich region of the pectins. 1H-N.m.r. analysis showed ∼30 percent of the disaccharides to be acetylated at a unique location. Two-dimensional 1H-1H homonuclear-correlation n.m.r. spectroscopy indicated this to be O-3 of galacturonic acid. During reaction in the HF, the disaccharides were quantitatively converted into the 3-O-acetylated and nonacetylated α-d-galactopyranosyluronic acid β-l-rhamnopyranose 1,2′:2,1′-dianhydride.

References (25)

  • J.M. Lau et al.

    Carbohydr. Res.

    (1985)
  • M.S. Kuo et al.

    Carbohydr. Res.

    (1986)
  • M.S. Kuo et al.

    Carbohydr. Res.

    (1986)
  • A.J. Mort et al.

    Carbohydr. Res.

    (1983)
  • M.F. Chaplin

    Anal. Biochem.

    (1982)
  • A.J. Mort

    Carbohydr. Res.

    (1983)
  • A.J. Mort et al.

    Anal. Biochem.

    (1983)
  • A. Debruyn et al.

    Carbohydr. Res.

    (1976)
  • R. Kasai et al.

    Tetrahedron

    (1979)
  • U. Kraska et al.

    Carbohydr. Res.

    (1976)
  • T. Fujiwara et al.

    Carbohydr. Res.

    (1979)
  • J. Defaye et al.

    Carbohydr. Res.

    (1988)
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