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Acid-Stable Ester Linkers for the Solid-Phase Synthesis of Immobilized Peptides.
ChemPlusChem ( IF 3.0 ) Pub Date : 2020-06-17 , DOI: 10.1002/cplu.202000246 Jan Pícha 1 , Miloš Buděšínský 1 , Katarína Mitrová 1 , Jiří Jiráček 1
ChemPlusChem ( IF 3.0 ) Pub Date : 2020-06-17 , DOI: 10.1002/cplu.202000246 Jan Pícha 1 , Miloš Buděšínský 1 , Katarína Mitrová 1 , Jiří Jiráček 1
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A series of N‐terminally Fmoc‐protected linkers of the general formula Fmoc‐X−CO−O−Y−COOH have been prepared, where X is −NH−CH2−CH2‐ or ‐p ‐(aminomethyl)phenyl‐ and Y is −(CH2)n− (n is 1 or 4) or ‐p ‐(methyl)phenyl‐. These linkers can easily be covalently attached via their C‐terminal carboxyl group to a resin bearing a free amino group. After cleavage of the N‐terminal Fmoc group, the linkers can be extended by standard solid‐phase peptide synthesis techniques. These ester linkers are acid‐stable and resistant to the base‐mediated diketopiperazine formation that often occurs during the synthesis of ester‐bound peptides; they are stable at neutral pH in aqueous buffers for days but can be effectively cleaved with 0.1 m NaOH or aq. ammonia within minutes or hours, respectively. These properties make these ester handles well suited for use as linkers for the solid‐phase peptide synthesis of immobilized peptides when the stable on‐resin immobilization of the peptides and the testing of their biological properties in aqueous buffers at neutral pH are necessary.
中文翻译：
固定肽段固相合成的酸稳定酯连接基。
已经制备了一系列由Fmoc-X-CO-O-Y-COOH组成的N末端受Fmoc保护的连接基，其中X是-NH-CH 2 -CH 2-或-p-（氨基甲基）苯基-并且Y为−（CH 2）n −（n为1或4）或-p-（甲基）苯基- 这些接头可以很容易地通过其C末端羧基与带有游离氨基的树脂共价连接。切割N端Fmoc基团后，可以通过标准固相肽合成技术扩展接头。这些酯连接基是酸稳定的，并且对酯键合肽合成过程中经常发生的碱基介导的二酮哌嗪形成具有抵抗力。它们在中性pH下在水性缓冲液中稳定几天，但可以用0.1 m NaOH或aq水溶液有效裂解。分别在几分钟或几小时内注入氨。
更新日期：2020-06-17
中文翻译：
固定肽段固相合成的酸稳定酯连接基。
已经制备了一系列由Fmoc-X-CO-O-Y-COOH组成的N末端受Fmoc保护的连接基，其中X是-NH-CH 2 -CH 2-或-p-（氨基甲基）苯基-并且Y为−（CH 2）n −（n为1或4）或-p-（甲基）苯基- 这些接头可以很容易地通过其C末端羧基与带有游离氨基的树脂共价连接。切割N端Fmoc基团后，可以通过标准固相肽合成技术扩展接头。这些酯连接基是酸稳定的，并且对酯键合肽合成过程中经常发生的碱基介导的二酮哌嗪形成具有抵抗力。它们在中性pH下在水性缓冲液中稳定几天，但可以用0.1 m NaOH或aq水溶液有效裂解。分别在几分钟或几小时内注入氨。
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