Letter | Published:

Some Tetrahydropyranyl Derivatives of Glycine, Serine and Urea

Nature volume 192, pages 10691070 (16 December 1961) | Download Citation

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Abstract

THE provision of model compounds containing amino-acids or their analogues attached to sugars is of importance in evaluating the stability of the numerous types of carbohydrate-peptide linkages theoretically possible in mucoproteins. The ability of 2,3-dihydropyran to condense with —OH, —SH, and —NH2 groupings suggested a route to the glycosidically linked model compounds. The tetrahydropyran-2-yl derivatives so formed had the added advantage that the lability of the glycosidic linkage could be investigated without attendant complications such as acyl migration under alkaline conditions or Amadori re-arrangement catalysed by acid which might ensue in the presence of a hydroxyl substituent at C–2 of the pyran ring.

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  1. Chemistry Department, The University, Edgbaston, Birmingham, 15.

    • S. M. AMIR
    • , M. Z. ATASSI
    • , S. A. BARKER
    • , J. S. BRIMACOMBE
    •  & M. C. KEITH

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https://doi.org/10.1038/1921069a0

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