期刊
JOURNAL OF ORGANIC CHEMISTRY
卷 80, 期 14, 页码 7058-7065出版社
AMER CHEMICAL SOC
DOI: 10.1021/acs.joc.5b00890
关键词
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资金
- Thailand Research Fund [DPG5780002]
- Thai government under the Project for Establishment of Comprehensive Center for Innovative Food, Health Products and Agriculture [TKK2555]
Sugar-derived cyclic beta-amino acids are important building blocks for designing of foldamers and other biornimetic structures. We report herein the first synthesis of a C-activated N-Fmoc-protected trans-(2S,3S)-3-aminotetrahydrofuran-2-carboxylic acid as a building block for Fmoc solid phase peptide synthesis. Starting from 2-deoxy-D-ribose, the product is obtained in a 6.796 overall yield following an 11-step reaction sequence. The tetrahydrofuran amino acid is used as a building block for a new peptide nucleic acid (PNA), which exhibits excellent DNA binding affinity with high specificity. It also shows preference for binding to DNA over RNA and specifically in the antiparallel orientation. In addition, the presence of the hydrophilic tetrahydrofuran ring in the PNA structure reduces nonspecific interactions and self-aggregation, which is a common problem in PNA due to its hydrophobic nature.
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