PyHOPO的合成、结构证实及其在固相肽合成中外消旋化还原中的应用

IF 1.5 4区化学 Q3 CHEMISTRY, ORGANIC

Tetrahedron Letters Pub Date : 2025-03-10 DOI:10.1016/j.tetlet.2025.155520

Kwazi Masuku , Anamika Sharma , Sikabwe Noki , Sizwe Zamisa , Ayman El-Faham , Beatriz G. de la Torre , Fernando Albericio

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引用次数: 0

摘要

本研究合成了PyHOPO，并用单射线XRD对其进行了表征。晶体结构明确地证实了P-O-N键而不是P-O-C键的存在。HOPO向PyHOPO的转化延长了NO键的长度，从而改变了电子密度分布，这可以通过静电作图来证明。这突出了磷原子向HOPO基团提供电子的性质。利用PyHOPO制备了h - tyrr - ser - ser - ph - leu - nh2五肽。然后对PyHOPO进行消旋化研究。研究了Ser、His和Cys在三肽(gly - x - ph - nh2；（X = Ser, His, Cys）。本研究发现，以PyHOPO作为偶联剂时，三种情况均未发生外消旋反应。

本文章由计算机程序翻译，如有差异，请以英文原文为准。

Synthesis and Structural Confirmation of PyHOPO and its Applicability in Racemization Reduction in Solid-Phase Peptide Synthesis

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Synthesis and Structural Confirmation of PyHOPO and its Applicability in Racemization Reduction in Solid-Phase Peptide Synthesis

In the current work, PyHOPO was synthesized and well characterized by single ray XRD. The crystal structure unambiguously confirmed the presence of a P-O-N bond rather than a P-O-C bond. The conversion of HOPO to PyHOPO elongates the NO bond length thereby changing the electron density distribution, as evidenced by electrostatic mapping. This highlights the phosphorus atom's electron-donating nature toward the HOPO moiety. PyHOPO was used to prepare pentapeptide H-Tyr-Ser-Ser-Phe-Leu-NH₂. PyHOPO was then evaluated for racemization study. Racemization was studied in the case of Ser, His and Cys upon incorporation in a tripeptide (Gly-X-Phe-NH₂; where X = Ser, His, Cys). For the study, it was found that there was no racemization in all the three cases when PyHOPO was used as coupling reagent.

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来源期刊

Tetrahedron Letters 化学-有机化学

CiteScore

3.50

自引率

5.60%

发文量

521

审稿时长

28 days

期刊介绍： Tetrahedron Letters provides maximum dissemination of outstanding developments in organic chemistry. The journal is published weekly and covers developments in techniques, structures, methods and conclusions in experimental and theoretical organic chemistry. Rapid publication of timely and significant research results enables researchers from all over the world to transmit quickly their new contributions to large, international audiences.