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首页> 外文期刊>Chemistry: A European journal >2-Methoxy-4-methylsulfinylbenzyl: A Backbone Amide Safety-Catch Protecting Group for the Synthesis and Purification of Difficult Peptide Sequences
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2-Methoxy-4-methylsulfinylbenzyl: A Backbone Amide Safety-Catch Protecting Group for the Synthesis and Purification of Difficult Peptide Sequences

机译：2-甲氧基-4-甲基亚磺酰基苄基：合成和纯化困难的肽序列的骨干酰胺安全保护基团。

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摘要

The use of 2-methoxy-4-methylsulfinylbenzyl (Mmsb) as a new backbone amide-protecting group that acts as a safety-catch structure is proposed. Mmsb, which is stable during the elongation of the sequence and trifluoroacetic acid-mediated cleavage from the resin, improves the synthetic process as well as the properties of the quasi-unprotected peptide. Mmsb offers the possibility of purifying and characterizing complex peptide sequences, and renders the target peptide after NH4I/TFA treatment and subsequent ether precipitation to remove the cleaved Mmsb moiety. First, the difficult peptide sequence H-(Ala)(10)-NH2 was selected as a model to optimize the new protecting group strategy. Second, the complex, bioactive Ac-(RADA)(4)-NH2 sequence was chosen to validate this methodology. The improvements in solid-phase peptide synthesis combined with the enhanced solubility of the quasi-unprotected peptides, as compared with standard sequences, made it possible to obtain purified Ac-(RADA)(4)-NH2. To extend the scope of the approach, the challenging A(1-42) peptide was synthesized and purified in a similar manner. The proposed Mmsb strategy opens up the possibility of synthesizing other challenging small proteins.
机译：有人提出使用2-甲氧基-4-甲基亚磺酰基苄基（Mmsb）作为一种新的主​​链酰胺保护基，该基团起着安全捕获结构的作用。 Mmsb在序列延长和三氟乙酸介导的树脂裂解过程中保持稳定，可改善合成过程以及准未保护肽的性质。 Mmsb提供了纯化和表征复杂肽序列的可能性，并在NH4I / TFA处理以及随后的醚沉淀以去除裂解的Mmsb部分后提供了目标肽。首先，选择困难的肽序列H-（Ala）（10）-NH2作为模型，以优化新的保护基策略。其次，选择复杂的生物活性Ac-（RADA）（4）-NH2序列来验证该方法。与标准序列相比，固相肽合成的改进与准未保护肽的溶解度提高相结合，使得有可能获得纯化的Ac-（RADA）（4）-NH2。为了扩展该方法的范围，以相似的方式合成并纯化了具有挑战性的A（1-42）肽。拟议的Mmsb策略为合成其他具有挑战性的小蛋白开辟了可能性。

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