Tosyl 및 Acetyl화된 Poly-β(1,4)-N-acetyl-D-glucosamine 유도체의 합성과 특성에 관한 연구

성용길; 장광태

Polymer(Korea), Vol.21, No.6, 921-925, November, 1997

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Tosyl 및 Acetyl화된 Poly-β(1,4)-N-acetyl-D-glucosamine 유도체의 합성과 특성에 관한 연구

Synthesis and Characterization of Tosylated and Acetylated Poly-β(1,4)-N-acetyl-D-glucosamine Derivatives

성용길, 장광태

초록

Poly-β(1,4)-N-acetyl-B-glucosamine은 천연 chitin을 4% NaOH 용액과 10% HCI 용액을 이용하여 정제하였다. Tosylation 과정에서는 pyranose 고리에 대하여 15몰비의 tosyl chloride(T_s)를 이용하였으며 tosylated chitin(T_s-chitin)은 고분자의 1차 알코을 위치에 tosylation시켜 합성하였고 acetylation 과정에서는 2차 알코올기의 반웅성을 없애기 위해 무수초산을 이용하여 acetylation시켰다. 이렇게 얻어진 아세틸화된 T_s-chitin에 항암성 의약인 3-(9-acridinyl-amino)-5-(hydroxymethyl )aniline(AHMA)를 도입시켜 chitin-AHMA를 합성하였다. 합성된 고분자는 FT-IR, ¹³C-NMR 및 원소 분석으로 확인하였다.

Poly-β(1,4)-N-acetyl-D-glucosamine was purified by natural chitin of 4% NaOH solution and 10% HCI solution. Tosylation was proceeded by tosyl chloride (T_s) of 15 mole equivalent to pyranose ring. Tosylated chitin (T _s-chitin) was synthesized at the position of primary alcohol on the polymer. Acetylation was also proceeded by acetic anhydride in order to diminish the reactivity of the secondary alcohol of the synthesized T_s-chitin. Chitin-3-(9- acridinylamino)-5-(hydroxymethyl)aniline was synthesized from acetylated T_s-chitin introducing antitumor agent 3-(9-acridinylamino)-5-(hydroxymethyl) aniline. The synthesized polymers were characterized by FT-IR, ¹³C -NMR, and elemental analysis.

Keywords:3-(9-acridinylamino)-5-(hydroxymethyl) aniline(AHMA);tosylated chitin;acetylated chitin;chitin-AHMA

[References]

Muzzarelli RAA, Riccardo AA, "Chitin," Pergamon Press, Oxford, U.K. (1987)
Nishi N, Noguchi J, Tokura S, Shiota H, Polym. J., 11, 27 (1979)
Kaifa K, Nishi N, Komai T, Somorin O, Polym. J., 13, 241 (1981)
Kurita K, Yoshino H, Yokota K, Motonai A, Satosh L, Ishii S, Nishimura SI, Macromolecules, 25, 3786 (1992)
Nisimura S, Kohgo O, Kurita K, Kuzuhara H, Macromolecules, 24, 4745 (1991)
Joo SM, Jang KT, Sung YK, J. Nat. Sci. Res. Inst., 15, 47 (1995)
Kim CH, Lee JW, Jung BO, Chang BK, Choi KS, Kim JJ, J. Korean Ind. Eng. Chem., 6(1), 130 (1995)
Lee JH, Nam KD, J. Korean Ind. Eng. Chem., 6(1), 29 (1995)
Kurita K, Yoshino H, Yokota K, Motonai A, Satosh L, Ishii S, Nishimura SI, Macromolecules, 25, 3786 (1992)
Macomick CL, Callais DA, Hutchiuson BH, Macromolecules, 18, 2394 (1985)
Kurita K, Yoshiyuki K, Satoshi I, Nishimura SI, Macromolecules, 23, 2894 (1985)
Hwang FS, Hogen-Esch TE, Macromolecules, 26, 3156 (1993)
Kurita K, Yoshida A, Kouama Y, Macromolecules, 21, 1579 (1993)
Su TL, Chou TC, Kim JY, Huang JT, Ciszewska G, Ren WY, Otter GM, Sirotnak FM, Watanabe KA, J. Med. Chem., 38, 3226 (1995)

[Referenced By]

[1] Muzzarelli RAA, Riccardo AA, "Chitin," Pergamon Press, Oxford, U.K. (1987)

[2] Nishi N, Noguchi J, Tokura S, Shiota H, Polym. J., 11, 27 (1979)

[3] Kaifa K, Nishi N, Komai T, Somorin O, Polym. J., 13, 241 (1981)

[4] Kurita K, Yoshino H, Yokota K, Motonai A, Satosh L, Ishii S, Nishimura SI, Macromolecules, 25, 3786 (1992)

[5] Nisimura S, Kohgo O, Kurita K, Kuzuhara H, Macromolecules, 24, 4745 (1991)

[6] Joo SM, Jang KT, Sung YK, J. Nat. Sci. Res. Inst., 15, 47 (1995)

[7] Kim CH, Lee JW, Jung BO, Chang BK, Choi KS, Kim JJ, J. Korean Ind. Eng. Chem., 6(1), 130 (1995)

[8] Lee JH, Nam KD, J. Korean Ind. Eng. Chem., 6(1), 29 (1995)

[9] Kurita K, Yoshino H, Yokota K, Motonai A, Satosh L, Ishii S, Nishimura SI, Macromolecules, 25, 3786 (1992)

[10] Macomick CL, Callais DA, Hutchiuson BH, Macromolecules, 18, 2394 (1985)

[11] Kurita K, Yoshiyuki K, Satoshi I, Nishimura SI, Macromolecules, 23, 2894 (1985)

[12] Hwang FS, Hogen-Esch TE, Macromolecules, 26, 3156 (1993)

[13] Kurita K, Yoshida A, Kouama Y, Macromolecules, 21, 1579 (1993)

[14] Su TL, Chou TC, Kim JY, Huang JT, Ciszewska G, Ren WY, Otter GM, Sirotnak FM, Watanabe KA, J. Med. Chem., 38, 3226 (1995)