| 高云霞,张家彬.化学通报,2025,88(12):1340-1344. |
| 一种糖氨基酸的可扩展合成及其在SARS-CoV-2 糖肽构建中的应用 |
| Scalable Synthesis of an N-Glycosylated Asparagine Building Block and Its application in SARS-CoV-2 Glycopeptide Synthesis |
| 投稿时间：2025-06-16 修订日期：2025-08-24 |
| DOI： |
| 中文关键词: 规模化合成 糖氨基酸合成砌块 Fmoc-Asn(Ac3GlcNAc)-OH SARS-CoV-2糖肽 |
| 英文关键词:Scalable synthesis, Glycosylated amino acid building block, Fmoc-Asn(Ac3/GlcNAc)-OH, SARS-CoV-2 glycopeptide |
| 基金项目: |
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| 摘要点击次数: 92 |
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| 中文摘要: |
| 开发一种高效、可规模化生产的Fmoc-Asn（Ac3GlcNAc）-OH合成方法，以解决N-糖肽核心砌块规模化制备的难题，并成功应用于SARS-CoV-2糖肽的固相合成。以廉价易得的50 g乙酰氨基葡萄糖为起始原料，凭借仅需重结晶的简易纯化技术，成功合成20 g高纯度关键糖氨基酸合成砌块Fmoc-Asn（Ac3GlcNAc）-OH，提升了合成效率。进一步将该砌块通过固相肽合成（SPPS）技术引入SARS-CoV-2糖肽序列，经高效液相色谱（HPLC）及质谱（MS）验证，最终以22%的总产率获得119.6 mg目标糖肽。该方法操作简便、产率高，为糖蛋白功能研究及抗病毒糖肽疫苗的开发提供了重要的合成基础。 |
| 英文摘要: |
| An efficient and scalable synthesis method of Fmoc-Asn (Ac3GlcNAc)-OH was developed to address the challenge of large-scale preparation of N-glycopeptide core building blocks, and was successfully applied to the solid-phase synthesis of SARS-CoV-2 glycopeptide. Using 50 g of inexpensive and readily available N-acetylglucosamine as the starting material, 20 g of the high-purity key glycosylated amino acid building block Fmoc-Asn(Ac3GlcNAc)-OH was successfully synthesized through a simple purification technique that only required recrystallization, thereby enhancing the synthetic efficiency. Subsequently, this building block was incorporated into the SARS-CoV-2 glycopeptide sequence via solid-phase peptide synthesis (SPPS) technology. After validation by high-performance liquid chromatography (HPLC) and mass spectrometry (MS), the target glycopeptide was obtained in a total yield of 22%, amounting to 119.6 mg. This method is operationally simple, scalable, and high-yielding, providing a solid synthetic foundation for glycoprotein functional studies and the development of antiviral glycopeptide vaccines. |
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