Homologated amino acids with three vicinal fluorines positioned along the backbone: development of a stereoselective synthesis.
Homologated amino acids with three vicinal fluorines positioned along the backbone: development of a stereoselective synthesis.
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DOI：
10.3762/bjoc.13.228
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发表时间：
2017
影响因子：
2.7
通讯作者：
Hunter L
中科院分区：
文献类型：
--
作者：
Cheerlavancha R;Ahmed A;Leung YC;Lawer A;Liu QQ;Cagnes M;Jang HC;Hu XG;Hunter L
骨架延伸氨基酸在肽和蛋白质科学中具有多种潜在应用，特别是如果氨基酸的几何形状是可控的。在这里，我们描述了合成的δ-氨基酸，含有三个相邻的C-F键定位沿着骨干。最终成功的合成方法是通过研究几种基于亲电和亲核化学的方法而出现的。我们表明，不同的非对映异构体的氟化δ-氨基酸在溶液中采用不同的构象，这表明这些分子可能具有价值的形状控制的积木在肽科学的未来应用。
Backbone-extended amino acids have a variety of potential applications in peptide and protein science, particularly if the geometry of the amino acid is controllable. Here we describe the synthesis of δ-amino acids that contain three vicinal C–F bonds positioned along the backbone. The ultimately successful synthetic approach emerged through the investigation of several methods based on both electrophilic and nucleophilic fluorination chemistry. We show that different diastereoisomers of this fluorinated δ-amino acid adopt distinct conformations in solution, suggesting that these molecules might have value as shape-controlled building blocks for future applications in peptide science.
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影响因子：
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作者：
GAO, Y;HANSON, RM;SHARPLESS, KB
通讯作者：
SHARPLESS, KB
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Roberts, Richard S.
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