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| 一种非天然六元环状氨基酸衍生物及其类似物的合成 |
| Synthesis of An Unnatural Six-Membered Cyclic Amino Acid Derivative and Its Analogue |
| 投稿时间：2025-03-11 修订日期：2025-04-07 |
| DOI： |
| 中文关键词: 非天然氨基酸 氨基酸衍生物 六元环状氨基酸 2-哌啶甲酸 氧杂六元环 |
| 英文关键词:unnatural amino acids, amino acid derivative, six-membered cyclic amino acid, pipecolic acid, six-membered oxygen-containing ring. |
| 基金项目:上海市浦江人才计划(18PJ1402200)和中央高校基本科研业务费专项资金(222201717003, JKVJ1241010,) |
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| 中文摘要: |
| 为突破天然氨基酸结构及其所携带的官能团的局限性，提高蛋白质多样性和功能性，结构多样、官能团丰富的非天然氨基酸的合成变得愈发重要。大部分已知的天然氨基酸和非天然氨基酸多以链状结构为主，然而，环状非天然氨基酸的合成研究相对较少，因此探索结构新颖的非天然环状氨基酸及其衍生物的合成方法具有十分重要的意义。本文以2-萘胺为主要原料，经过六步反应以接近20%的总收率合成了一种含有2-哌啶甲酸结构的非天然六元环状氨基酸衍生物，该产物不仅含有氮杂六元环，而且具有两个连续的碳手性中心和一个芳基烯基手性轴，结构新颖，在功能性蛋白质的合成中具有潜在的应用前景。 |
| 英文摘要: |
| The synthesis of structurally diverse unnatural amino acids bearing various functional groups has become increasingly important, as it helps to overcome the limitations of the structures of natural amino acids and the functional groups they carry, and to enhance the diversity and functionality of proteins. Most of the known natural and unnatural amino acids predominantly feature linear structures, in contrast, less attention has been devoted to the synthesis of cyclic unnatural amino acids. Therefore, it is important to develop new methods for the synthesis of structurally novel cyclic unnatural amino acids and their derivatives. Herein, we report the synthesis of an unnatural six-membered cyclic amino acid derivative containing a 2-piperidinecarboxylic acid structure in a total yield of 20%, through a six-step synthetic route, by using 2-naphthylamine as the starting material. This compound not only bears a six-membered nitrogen-containing ring, but also features two consecutive carbon stereocenters and an aryl-alkenyl chiral axis, presenting a novel structure with potential applications in the synthesis of functional proteins. |
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