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Int J Biol Macromol. 2017 Oct;103:202-207. doi: 10.1016/j.ijbiomac.2017.05.070. Epub 2017 May 17.

Preparation and characterization of amidated derivatives of alginic acid.

Author information

1
Institute of Animal Science, VÚŽV v.v.i., Přátelství 815, Prague 22 Uhříněves, 104 00, Czech Republic. Electronic address: taubner.tomas@vuzv.cz.
2
Institute of Animal Science, VÚŽV v.v.i., Přátelství 815, Prague 22 Uhříněves, 104 00, Czech Republic.
3
Department of Carbohydrates and Cereals, ICT Prague, Technická 5, Prague 6 Dejvice, 166 28, Czech Republic.

Abstract

Alginic acid is a suitable material for modification to prepare new derivatives because of presence of its carboxyl groups. The high content of carboxyl groups over the entire length of its chain renders it an easily modifiable material with a possibility of achieving a high degree of substitution in the prepared derivatives. The salt of alginic acid (sodium alginate) is readily commercially available and is widely used in many branches of chemistry. Alginic acid was thus selected as the substrate for amidation. The amidation used two-steps: methyl esterification followed by amino-de-alkoxylation. The aim of this study was to prepare highly substituted derivatives with different polysaccharide chain characteristics. As such, the alginic acid was modified by the two-step amidation based on the esterification of the alginic acid carboxyl groups by reaction with methanol and further amino-de-alkoxylation (aminolysis) of the obtained methyl ester with amidation reagents (n-alkylamines, hydrazine and hydroxylamine). The purity and substitution degree of the prepared derivatives were monitored by vibration spectroscopic methods (FTIR and FT Raman) and organic elemental analysis. These analytical methods confirmed the preparation of highly or moderately substituted N-alkylamides, hydrazide and hydroxamic acid of alginic acid.

KEYWORDS:

Alginate; Alginic acid; Amino-de-alkoxylation (aminolysis)

PMID:
28526341
DOI:
10.1016/j.ijbiomac.2017.05.070
[Indexed for MEDLINE]

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