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Synthesis of H-Lys-Lys-Gly-OH Tripeptide and Study of Its Acute Toxicity
Pharmaceutical Chemistry Journal ( IF 0.9 ) Pub Date : 2020-11-27 , DOI: 10.1007/s11094-020-02296-7
O. A. Popova , N. D. Bunyatyan , G. M. Bobizoda , M. Samiev , A. B. Prokof’ev , V. A. Evteev , L. N. Sernov

Tripeptide H-Lys-Lys-Gly-OH was synthesized. Its toxic properties and biological activity were studied. The tripeptide was synthesized by extending the peptide chain from the C-terminus by synthesizing N2, N6-dicarbobenzoxylysine [N2,N6-(Cbz)2Lys] and N6-carbobenzoxylysine (N6-CbzLys) methyl ester hydrochloride and condensing them by the mixed anhydride method to produce the methyl ester of N2,N6-(Cbz)2Lys-N6-CbzLys. The next step in the tripeptide synthesis consisted of obtaining glycine benzyl ester (Gly-OBzl) hydrochloride and condensing it with N2,N6-(Cbz)2Lys-N6-CbzLys hydrazide to produce the protected target tripeptide Z-Lys(Z)-Lys-Gly-OBzl. The last step consisted of removing the protection using hydrogenolysis over Ni-Re catalyst. Test results showed that the synthesized tripeptide had low toxicity.



中文翻译:

H-Lys-Lys-Gly-OH三肽的合成及其急性毒性研究

合成三肽H-Lys-Lys-Gly-OH。研究了它的毒性和生物学活性。通过合成N 2N 6-二碳代苄氧赖氨酸[ N 2N 6-(Cbz)2 Lys]和N 6-碳代苄氧赖氨酸(N 6 -CbzLys)甲酯盐酸盐,从C末端延伸肽链来合成三肽并通过混合酸酐法将其缩合以生成N 2N 6-(Cbz)2 Lys- N 6的甲酯-CbzLys。三肽合成的下一步包括获得甘氨酸苄基酯(Gly-OBzl)盐酸盐并将其与N 2N 6-(Cbz)2 Lys- N 6 -CbzLys酰肼缩合以生成受保护的目标三肽Z -Lys(Z)-Lys-Gly-OBzl。最后一步包括在Ni-Re催化剂上使用氢解作用去除保护层。试验结果表明,合成的三肽毒性低。

更新日期:2020-11-27
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