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在 SPPS 中使用 Npb-OH 光解保护基团合成环肽。

Synthesis of Cyclic Peptides in SPPS with Npb-OH Photolabile Protecting Group.

机构信息

Institute of Radiation Medicine, Beijing 100850, China.

出版信息

Molecules. 2022 Mar 29;27(7):2231. doi: 10.3390/molecules27072231.

DOI:10.3390/molecules27072231
PMID:35408630
原文链接:https://pmc.ncbi.nlm.nih.gov/articles/PMC9000773/
Abstract

Significant efforts have been made in recent years to identify more environmentally benign and safe alternatives to side-chain protection and deprotection in solid-phase peptide synthesis (SPPS). Several protecting groups have been endorsed as suitable candidates, but finding a greener protecting group in SPPS has been challenging. Here, based on the 2-(-nitrophenyl) propan-1-ol (Npp-OH) photolabile protecting group, a structural modification was carried out to synthesize a series of derivatives. Through experimental verification, we found that 3-(-Nitrophenyl) butan-2-ol (Npb-OH) had a high photo-release rate, high tolerance to the key conditions of Fmoc-SPPS (20% piperidine DMF alkaline solution, and pure TFA acidic solution), and applicability as a carboxyl-protective group in aliphatic and aromatic carboxyl groups. Finally, Npb-OH was successfully applied to the synthesis of head-tail cyclic peptides and side-chain-tail cyclic peptides. Moreover, we found that Npb-OH could effectively resist diketopiperazines (DKP). The α-H of Npb-OH was found to be necessary for its photosensitivity in comparison to 3-(-Nitrophenyl)but-3-en-2-ol (Npbe-OH) during photolysis-rate verification.

摘要

近年来，人们在寻找更环保、更安全的固相多肽合成（SPPS）中侧链保护和脱保护的替代方法方面做出了巨大努力。已经有几种保护基被认为是合适的候选者，但在 SPPS 中找到更环保的保护基一直具有挑战性。在这里，基于 2-(-硝基苯基)丙-1-醇（Npp-OH）光解保护基，进行了结构修饰以合成一系列衍生物。通过实验验证，我们发现 3-(-硝基苯基)丁-2-醇（Npb-OH）具有很高的光释放率、对 Fmoc-SPPS 的关键条件（20%哌啶 DMF 碱性溶液和纯 TFA 酸性溶液）的高耐受性，以及作为脂肪族和芳香族羧酸的羧基保护基的适用性。最后，Npb-OH 成功应用于头尾环肽和侧链尾环肽的合成。此外，我们发现 Npb-OH 可以有效抵抗二酮哌嗪（DKP）。与 3-(-硝基苯基)丁-3-烯-2-醇（Npbe-OH）相比，在光解速率验证过程中发现 Npb-OH 的α-H 对其光敏感性是必要的。

https://cdn.ncbi.nlm.nih.gov/pmc/blobs/080e/9000773/b03901839914/molecules-27-02231-sch010.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/080e/9000773/3edc6365d975/molecules-27-02231-sch001.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/080e/9000773/2d39013d1f7e/molecules-27-02231-sch002.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/080e/9000773/862c2392f0a4/molecules-27-02231-sch003.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/080e/9000773/bde16128b60a/molecules-27-02231-sch004.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/080e/9000773/c188fae4fe99/molecules-27-02231-sch005.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/080e/9000773/3e675ba27b2a/molecules-27-02231-sch006.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/080e/9000773/880b2a0585de/molecules-27-02231-sch007.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/080e/9000773/60e89c68dc92/molecules-27-02231-sch008.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/080e/9000773/8fd3e0a90180/molecules-27-02231-g001.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/080e/9000773/b082929975cc/molecules-27-02231-sch009.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/080e/9000773/b03901839914/molecules-27-02231-sch010.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/080e/9000773/3edc6365d975/molecules-27-02231-sch001.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/080e/9000773/2d39013d1f7e/molecules-27-02231-sch002.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/080e/9000773/862c2392f0a4/molecules-27-02231-sch003.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/080e/9000773/bde16128b60a/molecules-27-02231-sch004.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/080e/9000773/c188fae4fe99/molecules-27-02231-sch005.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/080e/9000773/3e675ba27b2a/molecules-27-02231-sch006.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/080e/9000773/880b2a0585de/molecules-27-02231-sch007.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/080e/9000773/60e89c68dc92/molecules-27-02231-sch008.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/080e/9000773/8fd3e0a90180/molecules-27-02231-g001.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/080e/9000773/b082929975cc/molecules-27-02231-sch009.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/080e/9000773/b03901839914/molecules-27-02231-sch010.jpg

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本文引用的文献

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