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Chemistry and Industry of Forest Products ›› 2016, Vol. 36 ›› Issue (2): 71-78.doi: 10.3969/j.issn.0253-2417.2016.02.011

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Preparation and Application of Tripeptide-cellulose Ester

LI Yang1,2, ZHU Jin-ke1, LI Lian-jie1, JIANG Deng-gao1   

  1. 1. School of Chemical Engineering and Energy, Zhengzhou University, Zhengzhou 450001, China;
    2. Henan Institute for Food and Drug Control, Zhengzhou 450003, China
  • Received:2015-02-15 Online:2016-04-25 Published:2016-04-26

Abstract: Tripeptide-cellulose ester (TPC) was synthesized by sequent acyl chlorination, esterification, peptide elongation and amino modification using microcrystalline cellulose as raw material and N-(9-fluorenylmethoxycarbonyl)-L-proline(FMOC-L-Pro-OH), N-(9-fluorenylmethoxycarbonyl)-L-valinamide-L-phenylalanine(FMOC-L-Val-L-Phe-OH), 3,5-dinitrobenzoic acid as derivatization reagents. The experimental results showed that during the synthesis process, esterification, a key step, was performed firstly, and followed by the extension of peptide chain. The effects of various experimental factors on esterification and substitution degree (DS) were investigated. The optimal condition was described as that the mass concentration of avicel in LiCl/DMAc 20 g/L, the molar ratio of —C(O)Cl to the hydroxyl content of cellulose 3:1, reaction temperature 100 ℃ and reaction time 20 h. By the further peptide elongation and amino modification, the tripeptide-cellulose ester with DS 2.15 was synthesized. The structure and properties were then characterized by using Fourier transform infrared spectroscopy, elemental analysis, X-ray diffraction and thermogravimetric analysis. The results showed that the modification of peptide by 3,5-dinitrobenzoic acid was successful and the synthesis process was feasible. With the alteration of precipitants, the intramolecular hydrogen bond was different and the obtained derivatives had different characteristics and functionalities. The tripeptide-cellulose ester precipitated in methanol was good enteric-coating material with good shading effect and rapid disintegration, but the physiological toxicity needed further study. The tripeptide-cellulose ester (using water as the precipitant) could be coated onto silica gel to get a chiral stationary phase, which has a wider application than previous coated-cellulose chiral stationary phase. In addition, the stable chemical resistance of tripeptide-cellulose ester was particularly suitable for the mobile phase including tetrahydrofuran.

Key words: microcrystalline cellulose, peptide, derivatives, esterification, synthesis

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