酰胺键与三氟乙酸（20％）的不稳定性：合成，构象分析和机制的见解，以裂解的酰胺键包含β-Troponylhydrazino酸,ACS Omega

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酰胺键与三氟乙酸（20％）的不稳定性：合成，构象分析和机制的见解，以裂解的酰胺键包含β-Troponylhydrazino酸
ACS Omega ( IF 3.7 ) Pub Date : 2020-10-01 , DOI: 10.1021/acsomega.0c03729
Nihar Ranjan Dalabehera _{1,

2} , Sagarika Meher _{1,

2} , Bibhuti Bhusana Palai _{1,

2} , Nagendra K. Sharma _{1,

2}

Affiliation

稀三氟乙酸（TFA）酰胺键的不稳定性是罕见的化学事件。即使在纯TFA中，天然酰胺键也是稳定的，TFA是在固相支持的肽合成方法中从固相支持物中释放肽的试剂之一。在非天然肽组学中，探索了α-/β-肼基酸及其肽以合成N-氨基肽衍生物及其酰胺键在TFA中稳定（约100％）作为天然酰胺键。该报告描述了包含非苯甲酮天然肌钙蛋白支架的β-肼基酸类似物作为β-肌醇酰肼酸的合成。他们的杂二-/三肽与天然氨基酸的结构和构象研究表明2-氨基苯乙酰基残基参与氢键合。令人惊讶的是，通过形成新的杂环分子N，β-对苯二甲酰肼基肽的酰胺键可被TFA（〜20％）裂解。-对苯二甲酰基吡唑烷酮或对苯二甲酰基吡唑烷酮。Tropolone和相关化合物是出色的生物相容性发色团。因此，β-对苯二甲酰肼酸可用于调节肽结构，并被认为是氨基酸/肽的游离胺的有希望的发色酸敏感的保护基。它可以用于紫外可见分光光度计对游离胺基官能团的估计。

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Instability of Amide Bond with Trifluoroacetic Acid (20%): Synthesis, Conformational Analysis, and Mechanistic Insights into Cleavable Amide Bond Comprising β-Troponylhydrazino Acid

The instability of an amide bond with dilute trifluoroacetic acid (TFA) is a rare chemical event. The native amide bonds are stable even in the neat TFA, which is one of the reagents that releases the peptides from the solid support in the solid-supported peptide synthesis method. In the repertoire of unnatural peptidomics, α-/β-hydrazino acids and their peptides are explored for the synthesis of N-amino peptide derivatives, and their amide bonds are stable in TFA (∼100%) as natural amide bonds. This report describes the synthesis of a β-hydrazino acid analogue as β-troponylhydrazino acid, containing a nonbenzenoid natural troponyl scaffold. The structural and conformational studies of their hybrid di-/tripeptides with the natural amino acid show that the 2-aminotroponyl residue is involved in hydrogen bonding. Surprisingly, the amide bond of β-troponylhydrazino peptides is cleavable with TFA (∼20%) through the formation of a new heterocyclic molecule N-troponylpyrazolidinone or troponylpyrazolidinone. Tropolone and related compounds are excellent biocompatible chromophores. Hence, β-troponylhydrazino acid could be employed for tuning the peptide structure and considered a promising chromophoric acid-sensitive protecting group of a free amine of amino acids/peptides. It could be applied for the estimation of the free amine group functionality by a UV–vis spectrophotometer.

更新日期：2020-10-13

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