Summary
The hydrolytic stability of the ester bond of O-aminoacyl derivatives of N-acetylglucosamine, glucosamine (base), and methyl N-acetylneuraminate has been studied at pH 1–8. It has been shown that the stability of the O-aminoacyl derivatives of N-acetylglucosamine is comparable with that of the corresponding glucose derivatives. The presence of a free amino group in glucosamine leads to a considerable labilization of the ester bond. The ester bond of the O-aminoacyl derivatives of methyl N-acetylneuraminate is characterized by a very high lability, and this must be taken into account in working with biopolymers.
Similar content being viewed by others
References
V. A. Derevitskaya, V. M. Kalinevich, and N. K. Kochetkov, DAN SSSR,160, 596, 1965.
N. K. Kochetkov, V. A. Derevitskaya, and V. M. Kalinevich, Izv. AN SSSR, ser. khim.,3, 496, 1965.
N. K. Kochetkov, V. A. Derevitskaya, and L. M. Likhosherstov, Izv. AN SSSR, ser. khim.,4, 688, 1963.
N. K. Kochetkov, V. A. Derevitskaya, and L. M. Likhosherstov, Izv. AN SSSR, ser. khim.,2, 367, 1967.
Zh. V. Uspenskaya and V. L. Kretovich, Methods for the Quantitative Paper Chromatography of Sugars, Amino Acids, and Plants [in Russian], 59, Moscow, 1962.
Author information
Authors and Affiliations
Additional information
Khimiya Prirodnykh Soedinenii, Vol. 4, No. 1, pp. 28–32, 1968
Rights and permissions
About this article
Cite this article
Derevitskaya, V.A., Kalinevich, V.M. Hydrolytic stability of the ester bond in aminoacyl derivatives of N-acetylglucosamine, glucosamine, and N-acetylneuraminic acid. Chem Nat Compd 4, 22–24 (1968). https://doi.org/10.1007/BF00567756
Published:
Issue Date:
DOI: https://doi.org/10.1007/BF00567756