CAJ | 학술논문

目的：使用光敏感保护基和固相合成法制备Phakellistatin 13。方法使用二氢吡喃树脂作为固相载体，利用自行制备的光敏感保护基对苏氨酸进行保护并将其固定于树脂上。以该苏氨酸作为起始氨基酸，进行常规肽链组装，肽链组装完毕后通过光照脱去光敏感保护基，在固相上完成环合，切除后得到游离环肽。结果使用邻硝基乙苯一步制得了具有光敏感作用的2-（2-硝基苯基）-丙醇（Npp-OH），利用该保护基保护了苏氨酸羧基并借此完成了Phakellistatin 13的合成。终产物结构经高分辨质谱确证，表明该策略切实可行，为环肽的合成提供了有效的工具。结论 Npp保护基易于制备，保护和去保护收率高，对酸碱稳定，因此是一种优良的第三维保护基。利用该保护基，有效的完成了环肽的合成。
목적：사용광민감보호기화고상합성법제비Phakellistatin 13。방법사용이경필남수지작위고상재체，이용자행제비적광민감보호기대소안산진행보호병장기고정우수지상。이해소안산작위기시안기산，진행상규태련조장，태련조장완필후통과광조탈거광민감보호기，재고상상완성배합，절제후득도유리배태。결과사용린초기을분일보제득료구유광민감작용적2-（2-초기분기）-병순（Npp-OH），이용해보호기보호료소안산최기병차차완성료Phakellistatin 13적합성。종산물결구경고분변질보학증，표명해책략절실가행，위배태적합성제공료유효적공구。결론 Npp보호기역우제비，보호화거보호수솔고，대산감은정，인차시일충우량적제삼유보호기。이용해보호기，유효적완성료배태적합성。
Objective Preparation of the Phakellistatin 13 by using of solid-phase peptide synthesis method and photolabile protecting group. Methods By using of the DHP resin as the solid-phase supporter, a threonine derivative which was protected by the self-prepared photolabile protecting group was anchored to. The linear peptide was assembled via standard procedure with the threonine as the starting amino acid. After that, the photolabile protecting group was removed by UV irradiation, and the cyclization was completed while the peptide was still attached on the beads. The free cyclic peptide was then cut off by acid. Results The photolabile 2-(2-nitrophenyl)-propanol (Npp-OH) was synthesized in one step from o-nitroethylbenzene. With the Npp group, the carboxyl group of threonine was blocked and Phakellistatin 13 was synthesized. The Phakellistatin 13 was identified by high resolution mass spectrometry, indicated that the strategy is quite available, which offer an efficient method for cyclic peptide synthesis. Conclusion The Npp group had the advantages of easy prepared, high yields for protection and deprotection, be stable to the acidic and alkaline conditions, therefore it is an excellent third division protecting group. With this group, the cyclic peptide can be synthesized efficiently.