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Hydrolytic stability of the ester bond in aminoacyl derivatives of N-acetylglucosamine, glucosamine, and N-acetylneuraminic acid

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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.

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References

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Additional information

Khimiya Prirodnykh Soedinenii, Vol. 4, No. 1, pp. 28–32, 1968

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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

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Keywords

  • Glucosamine
  • Ester Bond
  • Amino Sugar
  • Hydrolytic Stability
  • Neuraminic Acid