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Some Tetrahydropyranyl Derivatives of Glycine, Serine and Urea

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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References

  1. Holland, G. F., and Cohen, L. A., J. Amer. Chem. Soc., 80, 3765 (1958).

    Article  CAS  Google Scholar 

  2. Ellis, G. P., Adv. in Carbohydrate Chem., 14, 70 (1959).

    Google Scholar 

  3. Brady, O. L., J. Chem. Soc., 756 (1931).

  4. Berry, H. K., and Cain, L., Arch. Biochem., 24, 179 (1949).

    CAS  PubMed  Google Scholar 

  5. Rydon, H. N., and Smith, P. W. G., Nature, 169, 922 (1952).

    Article  ADS  CAS  Google Scholar 

  6. Kaverzneva, V. E., and Kalis, E. D., Biokhimiya, 23, 92 (1958); 24, 1026 (1959).

    CAS  Google Scholar 

  7. Wolfrom, M. L., Schmetz, R. D., and Cavalieri, L. F., J. Amer. Chem. Soc., 71, 3518 (1949).

    Article  CAS  Google Scholar 

  8. Wood, G. F., and Sanders, H., J. Amer. Chem. Soc., 68, 2111 (1946).

    Article  Google Scholar 

  9. Benn, M. H., and Jones, A. S., J. Chem. Soc., 3837 (1960).

  10. Hirst, E. L., Hough, L., and Jones, J. K. N., J. Chem. Soc., 929 (1949).

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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

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