대칭형 및 비대칭형 Benzodiputeridine 유도체들의 합성과 (1)H NMR에 의한 구조 연구

이용희; 최종정; Yong Hee Lee; Jong Jueng Choi

Journal of the Korean Industrial and Engineering Chemistry, Vol.12, No.5, 590-594, August, 2001

Synthesis and Structure Investigation of Benzodiputeridine Derivatives having Symmetrical Form and Asymmetrical Form by (1)H NMR

이용희, 최종정^{1, †}

동아대학교 기초과학연구소, 부산 604-714
¹경남정보대학 공업화학과, 부산 617-701

Yong Hee Lee, and Jong Jueng Choi^{1, †}

Basic Science Research Institute, Dong-A University, Busan 604-714, Korea
¹Department of industrial Chemistry, Kyung Nam College of Information and Technology, Busan 617-701, Korea

E-mail:

초록

Turnover 산화환원 촉매인 인공플라빈효소를 구축하기 위해서 대칭형으로 이루어진 7,14-diethyl-3,10-dimethylbenzodiputeridine(5)와 3,10-dibenzyl-7,14-diethylbevzodiputeridine(9), 비대칭형으로 이루어진 7-benzyl-14-ethyl-3,10-dimethylbenzodiputeridine(17)의 벤조디프테리딘(Benzodiputeridine) 유도체들을 출발물질인 p-phenylenediamine과 p-nitroaniline으로부터 합성하였다. 대칭형인 벤조디프테리딘 유도체(5, 9)와 비대칭형인 벤조디프테리딘 유도체(17)을 (1)HNMR에 의한 구조분석 결과는 직선구조로 이루어져 있음을 알았다.

To construct artificial flavoenzymes s a turnover redox catalyst, Benzodiputeridine(BDP) derivatives, 7,14-diethyl-3,10-dimethylbenzodiputeridine(5) and 3,10-dibenzyl-7,14-diethylbenzodiputeridine(9) of the symmetrical form and 7-benzyl-14-ethyl-3, 10-dimethyl-benzodiputeridine(17) of the asymmetrical form, were synthesized from p-phenylenediamine nd p-nitroaniline as the starting material, respectively. In the tructure investigation by (1)HNMR, both symmetrical BDP(5, 9) and asymmmetrical BDP(17) were determined to gave a linear structure.

Keywords:benodiputeridine(BDP);symmetrical form;linear structure

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[1] Lehninger AL, "Principles of Biochemistry" Worth, New York (1982)

[2] Nielsen P, Rauschenbach P, Bacher A, Anal. Biochem., 130, 359 (1983)

[3] Miura R, Nishina Y, Ohta M, Biochem. Biophys. Res. Commun., 98, 830 (1976)

[4] Bruice TC, "Progress of Bioorganic Chemistry" Wiley, New York (1976)

[5] Bruice TC, Accounts Chem. Res., 13, 256 (1980)

[6] Yoneda F, Kakuma Y, Ichiba M, Shinomura K, J. Am. Chem. Soc., 98, 830 (1976)

[7] Bruice TC, Chan TW, Taulene JP, Yokoe I, J. Am. Chem. Soc., 99, 6713 (1977)

[8] Loechler EL, Hollocher TC, J. Am. Chem. Soc., 102, 7312 (1980)

[9] Yano Y, Nakazato M, Ohya E, J. Chem. Soc.-Perkin Trans. 2, 103, 7132 (1986)

[10] Yano Y, Kamishima H, Sutoh S, Iizuka K, J. Chem. Res.(S), 382 (1986)

[11] Yoneda F, Sakuma Y, Shinozuka K, J. Chem. Soc.-Perkin Trans. 1, 348 (1978)

[12] Yoneda F, Koga M, Yano Y, J. Chem. Soc.-Perkin Trans. 1, 1813 (1988)

[13] Seward EM, Hopkins RB, Diedrich F, J. Am. Chem. Soc., 112, 1783 (1990)

[14] Yano Y, Tamura N, 有機合成化學, 50(10), 899 (1992)

[15] Yoneda F, Koga M, Tanaka K, Yano Y, J. Heterocyclic. Chem., 26, 1221 (1989)