화학적 방법으로 변형된 탄수화물의 합성 및 특성

양수연, 서은성, 김병훈, 유선균, 조용익, 정상귀, 조성용, 최창남, 김도만

전남대학교 공업기술연구소

Synthesis and Characterization of Chemically Modified Carbohydrates

Soo-Yeon Yang, Eun-Sung Seo, Byung-Hun Kim, Sunkyun Yoo, Young-Ick Cho, Sang-Gwi Chung, Sung-Yong Cho, Chang-Nam Choi, Doman Kim

Engineering Research Institute, Chonnam National University

Introduction

Carbohydrates from natural sources are used for functional and non toxic biodegradable materials such as drug carriers. Modified polysaccharides are valuable for drug delivery system, wound healing, artficial muscles, and special inhibitors for the bacterial proliferation. Especially, dextran is widely used as biomedical materials because it contains primary glucopyranosyl residues and three hydroxyl groups per glucose residue in the structure. In this study, we synthesized and tested the activity of enzyme in the modified glucans as potential enzyme inhibitor.

Experimetals

Carboxymethyl dextarn (CMD; II) was synthesized as described previously [1]. Ketodextran, sulfated dextran and Iron-dextran complex were synthesized by reference method [2]. Chlorocarboxymethyldextran (CCMD; III) was prepared by chlorination of CMD using thionyl chloride. Carboxymethyl(n-propyl)amid dextran (CMPAD; IV) was synthesized by condensation of CCMD and n-propylamine. Charcterization was performed with FT-Infrared spectroscopy (Simatzu 8300). Dextran, n-propylamine and  thionyl chloride were purchased from Sigma-Aldrich Chemical Co.

Result and Discussion

Hydroxyl groups of dextran were converted to Iron-complex, 3-keto- carboxymethyl-, chlorocarboxymethyl-, and amid group, respectively. Carboxymethylation of hydroxyl groups of dextran(CD) proceeded as the reference-method [1]. Structures of products were analyzed by FT-IR spectroscopy. There are  peaks at ca.1300(□Fe…O), 1715(□C=O), 1070(□asym,O-S=O), 1140(□sym,O-S=O), 1736(□Cl-C=O), and 1620(□overlaped HNC=O) cm-1. Thermal characterization was studied with DSC. The inhibition for the dental plague forming enzyme by the modified oligosaccharides was examined using mutansucrase and dextransucrase. The inhibition of the enzyme was the highest in the presence of the iron-oligosaccharide complex.

Figure 1. Scheme of the synthesis of modified glucans

Figure 2. FT-IR spectrum of modified oligosaccharides;

(A) Oligosaccharide, (B) Sulfated oligosaccharide,

(C) Iron oligosaccharide complex.

Figure 3. Mutansucrase inhibition in the modified oligosaccharides;

(A) Mutansucrase + sucrose + buffer, (B) Mutansucrase + sucrose + Oligosaccharide, (C) Mutansucrase + Sucrose + Sulfated oligosaccharide, (D) Mutansucrase + sucrose + Iron-oligosaccharide complex

Figure 4. Dextransucrase inhibition in the modified oligosaccharides;

(A) Dextransucrase + sucrose + buffer, (B) Dextransucrase + sucrose + Oligosaccharide, (C) Dextransucrase + Sucrose + Sulfated oligosaccharide, (D) Dextransucrase + sucrose + Iron-oligosaccharide complex

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