Direct Biomimetic Synthesis of beta-Carboline Alkaloids from Two Amino Acids
Direct Biomimetic Synthesis of beta-Carboline Alkaloids from Two Amino Acids
复制标题
从两种氨基酸直接仿生合成β-咔啉生物碱
DOI：
10.1021/acs.joc.8b01668
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发表时间：
2018
影响因子：
3.6
通讯作者：
Wu An-Xin
中科院分区：
文献类型：
--
作者：
Wang Zi-Xuan;Xiang Jia-Chen;Cheng Yan;Ma Jin-Tian;Wu Yan-Dong;Wu An-Xin
酶模拟物在有机合成中日益重要的作用促使我们设计了一种新的由色氨酸和第二种氨基酸直接合成β-Caroline生物碱的仿生合成方法。这种新颖的一锅法利用了大量和容易获得的起始材料，因此提供了一种绿色和用户友好的替代传统方法，依赖于逐步合成。在分子碘和TFA的驱动下，脱羧基、脱氨基、Pictet-Spengler反应和氧化反应依次进行，将生物质氨基酸转化为具有增值价值的生物碱基序。
The increasing importance of enzyme mimics in organic synthesis inspired us to design a novel biomimetic synthesis of β-carboline alkaloids directly from tryptophan and a second amino acid. This novel one-pot protocol utilizes abundant and readily available starting materials and thus presents a green and user-friendly alternative to conventional methods that rely on stepwise synthesis. Driven by molecular iodine and TFA, decarboxylation, deamination, Pictet–Spengler reaction, and oxidation reactions proceeded sequentially, transforming biomass amino acids into value-added alkaloid motifs.