3-(芴甲氧羰基-氨基酸)-3,4-二氨基苯甲酸的一步合成法。
One-Step Synthesis of 3-(Fmoc-amino acid)-3,4-diaminobenzoic Acids.
作者信息
Chien Min-Cheng, Lin Yi Kai, Liao Yong, Chen Szu-Hsuan, Chen Yen-Wei, Liang Chien-Yu, Molakaseema Vijayasimha, Hsu Sodio C N, Lin Chun-Cheng, Chen Hui-Ting, Kao Chai-Lin
机构信息
Department of Medicinal and Applied Chemistry, Kaohsiung Medical University, Kaohsiung 807, Taiwan.
Department of Pharmacy, National Yang Ming Chiao Tung University, Taipei 112, Taiwan.
出版信息
ACS Omega. 2023 Oct 24;8(44):41855-41864. doi: 10.1021/acsomega.3c06640. eCollection 2023 Nov 7.
A one-step method for synthesizing 3-(Fmoc-amino acid)-3,4-diaminobenzoic acids was used to prepare preloaded diaminobenzoate resin. The coupling of free diaminobenzoic acid and Fmoc-amino acids gave pure products in 40-94% yield without any purification step in addition to precipitation except for histidine. For the proline residue, crude products were collected and used for solid-phase peptide synthesis to give a moderate yield of a pentapeptide. In addition, this method was used to prepare unusual amino acid derivatives, namely, (2-naphthyl) alanine and 6-aminohexanoic acid derivatives, in 50 and 65% yield, respectively.
采用一步法合成3-(Fmoc-氨基酸)-3,4-二氨基苯甲酸来制备预负载二氨基苯甲酸酯树脂。游离二氨基苯甲酸与Fmoc-氨基酸的偶联反应除组氨酸外，无需任何纯化步骤，仅通过沉淀即可得到产率为40 - 94%的纯产物。对于脯氨酸残基，收集粗产物并用于固相肽合成，得到了中等产率的五肽。此外，该方法还用于制备特殊氨基酸衍生物，即(2-萘基)丙氨酸和6-氨基己酸衍生物，产率分别为50%和65%。
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