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.
This is a preview of subscription content, access via your institution
Access options
Subscribe to this journal
Receive 51 print issues and online access
$199.00 per year
only $3.90 per issue
Rent or buy this article
Prices vary by article type
from$1.95
to$39.95
Prices may be subject to local taxes which are calculated during checkout
Similar content being viewed by others
References
Holland, G. F., and Cohen, L. A., J. Amer. Chem. Soc., 80, 3765 (1958).
Ellis, G. P., Adv. in Carbohydrate Chem., 14, 70 (1959).
Brady, O. L., J. Chem. Soc., 756 (1931).
Berry, H. K., and Cain, L., Arch. Biochem., 24, 179 (1949).
Rydon, H. N., and Smith, P. W. G., Nature, 169, 922 (1952).
Kaverzneva, V. E., and Kalis, E. D., Biokhimiya, 23, 92 (1958); 24, 1026 (1959).
Wolfrom, M. L., Schmetz, R. D., and Cavalieri, L. F., J. Amer. Chem. Soc., 71, 3518 (1949).
Wood, G. F., and Sanders, H., J. Amer. Chem. Soc., 68, 2111 (1946).
Benn, M. H., and Jones, A. S., J. Chem. Soc., 3837 (1960).
Hirst, E. L., Hough, L., and Jones, J. K. N., J. Chem. Soc., 929 (1949).
Author information
Authors and Affiliations
Rights and permissions
About this article
Cite this article
AMIR, S., ATASSI, M., BARKER, S. et al. Some Tetrahydropyranyl Derivatives of Glycine, Serine and Urea. Nature 192, 1069–1070 (1961). https://doi.org/10.1038/1921069a0
Issue Date:
DOI: https://doi.org/10.1038/1921069a0
This article is cited by
-
Synthesis of Glucopeptides
Nature (1964)
Comments
By submitting a comment you agree to abide by our Terms and Community Guidelines. If you find something abusive or that does not comply with our terms or guidelines please flag it as inappropriate.