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Cyclic peptide유도체들의 합성과 단백질 분해효소에 대한 저해활성 측정(Ⅰ)
강신원,신흥대,허남원,장태식,이호용 부산대학교 1990 자연과학논문집 Vol.49 No.-
Most of legume seeds contain serveral kinds of BBI-type inhibitors. They have similar amino acid residues around site. The P1 site amino acid residue in reactive site generally corresponds to the specificity of the congnate enzyme. It has also been noted the importance of P1 site amino acid residue in synthetic cyclic nonapetide derivatives which were related to active site of BBI. To obtain further understanding of the role of amino acid residues near the reactive site, 3 cyclic nonapeptides which are substituted analogues of GBI-Il were synthesized and the inhibition constants for some proteinases were calculated by dixon method. Antielastic fragment in GBI-Il(Ia) differ P2 site with that of soybean isoinhibitor C-Ⅱ, Ki of Ia for porcine pancreatic elastase was 48μM, ki of antitryptic fragment in LBI(Ib) for trypsin was 3.7μM, and tyr analogue (Ie) for chymtrypsin showed no inhibition but appeared low inhibitory activity for trypsin and elastase. To elucidate the relation between loop size and inhibitory activity, 3 cyclic pentapeptide analogues containing the each reactive site of Ala-ser, Lys-ser, and Try-ser were synthesized. These peptides possessed lower inhibitory activity toward proteinases, Ki of synthetic cyclic pentapeptides for elastase, trypsin, and chymotrypsin were 614μ, 278μM, and 128μM, respectively. Theseresults suggested that the P2 site of inhibitors contributed to react with the active site of some proteinases and the loop size were also important to react with enzymes.
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문성환,김종안,김경희,구자석,허남원,김동규,신흥대,강신원,Moon, Sung-Hwan,Kim, Jong-Ahn,Kim, Keung-Hee,Koo, Ja-Seok,Huh, Nam-Won,Kim, Dong-Kyu,Shin, Hong-Dae,Kang, Shin-Won 생화학분자생물학회 1987 한국생화학회지 Vol.20 No.4
페니실린 G와 펩타이드의 유리딘 유도체를 합성하여 쥐의 lymphoblastoma L5178Y 세포와 Staphylococcus aureus(IAM 3610) 그리고 Escherichia coli(ATCC 10536)에 대해서 생물 활성 실험을 행하였다. 본 연구에 이용된 합성 화합물들은 5'-amino-5'-deoxyuridine-penicillin G(14), 5'-amino-5'-deoxyuridine-cyclo (Phe-Asp) (15-I). 5's-amino-5'-deoxyuridine-cyclo (Phe-Glu) (15 -II), 5'-iodo-5'-amino-2', '3'-isopropylidene uridine-penicillin G (16), 5'-iodo-5'-amino-5'-deoxyuridine-penicilline G (17), 그리고 5'-deoxyuridine-penicilline G (19) 등을 사용하였다. 이들 각각의 $IC_{50}$ 값은 $18.0\;{\mu}g/ml$, $6.5\;{\mu}g/ml$, $6.5\;{\mu}g/ml$, $13.5\;{\mu}g/ml$, $6.5\;{\mu}g/ml$ 그러고 $9.0\;{\mu}g/ml$로 나타났다. 또한 (15-I)과 (17)의 MIC 값이 $6.25\;{\mu}g/ml$로 나타났다. 이러한 일차적인 결과는 유리딘이나 페니실린 또한 펩타이드가 conjugate 됨으로써 더욱더 생물활성을 개선시키는 결과를 보여 주고 있다. Six new uridine-conjugates of penicillin G and peptides have been prepared and evaluated against mouse lymphoblastoma L5178Y cells, Staphylococcus aureus(IAM 3610) and Escherichia coli(ATCC 10536). These include 5'-amino-5'-deoxyuridine-penicillin G(14), 5'-amino-5'-deoxyuridine-cyclo (Phe-Asp)(15-I). 5'-amino-5'-deoxyuridine-cyclo (Phe-Glu)(15-II), 5-iodo-5'-amino-2',3'-0-isopropylidene uridine- penicillin G(16), 5-iodo-5'-amino-5'-deoxyuridine-penicillin G(17), and 5'-deoxyuridine-penicillin G(19). $IC_{50}$ values were $18.0\;{\mu}g/ml,$ $6.5\;{\mu}g/ml,$. $6.5\;{\mu}g/ml,$ $13.5\;{\mu}g/ml$, $6.5\;{\mu}g/ml$ and $9.0\;{\mu}g/ml$, respectively. MIC values of (15-I) and (17) were $6.25\;{\mu}g/ml,$. These preliminary results support the thesis that the uridine conjugates of this type may require a naturally occurring moiety for improved efficacy.
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