Propylphosphonic Anhydride (T3P®) as Coupling Reagent for Solid‐Phase Peptide Synthesis,ChemistrySelect

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Propylphosphonic Anhydride (T3P®) as Coupling Reagent for Solid‐Phase Peptide Synthesis
ChemistrySelect ( IF 1.9 ) Pub Date : 2021-02-16 , DOI: 10.1002/slct.202100123
Othman Al Musaimi _{1,

2} , Richard Wisdom ₃ , Peter Talbiersky ₃ , Beatriz G. De La Torre ₂ , Fernando Albericio _{1,

4,

5}

Affiliation

Amidation is the predominant reaction within the pharmaceutical setting, and it is attracting greater attention due to the increased demand for therapeutic peptides. The high therapeutic efficacy and safety profile of peptides have placed these molecules in prime position within the pharmaceutical arena, which is reflected by these molecules receiving several approvals from various regulatory agencies each year. In this context, the demand for developing efficient strategies for peptide synthesis has also risen. Although propylphosphonic anhydride (T3P®), which has been recently proposed as a green coupling reagent, has shown good performance in solution, it has never been applied to solid‐phase peptide synthesis (SPPS). Here we test the use of T3P® for SPPS. Satisfactory yields were achieved with a mild activation protocol. Various green solvents were tested and proved to be compatible with this coupling reagent. Several commonly used reagents cause allergic reactions or are susceptible to explosion under certain conditions. To overcome these issues, we propose T3P® as a potential alternative coupling reagent in SPPS.

中文翻译：

丙基膦酸酐（T3P®）作为固相肽合成的偶联剂

酰胺化是药物领域的主要反应，由于对治疗性肽的需求增加，因此引起了越来越多的关注。肽的高治疗功效和安全性已将这些分子置于药学领域的首要位置，这反映在这些分子每年均获得各种监管机构的多项批准的情况下。在这种情况下，对开发用于肽合成的有效策略的需求也增加了。尽管最近被提议作为绿色偶联剂的丙基膦酸酐（T3P®）在溶液中表现出良好的性能，但从未将其用于固相肽合成（SPPS）。在这里，我们测试了T3P®在SPPS上的使用。使用温和的激活方案可达到令人满意的产量。测试了各种绿色溶剂，并证明与该偶联剂兼容。在某些条件下，几种常用的试剂会引起过敏反应或易于爆炸。为了克服这些问题，我们建议使用T3P®作为SPPS中潜在的替代偶联剂。

更新日期：2021-03-17

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