利用噁唑烷酮稠合吖環丙烷進行不對稱合成氟化胺基酸;Asymmetric Synthesis of Fluorinated Amino Acids via Ring-Opening of Oxazolidinone-Fused Aziridines

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题名:	利用噁唑烷酮稠合吖環丙烷進行不對稱合成氟化胺基酸;Asymmetric Synthesis of Fluorinated Amino Acids via Ring-Opening of Oxazolidinone-Fused Aziridines
作者:	陳弘哲;Chen, Hung-Che
贡献者:	化學學系
关键词:	噁唑烷酮;吖環丙烷;氟開環反應;Oxazolidinone;Aziridines;Fluoride Ring-Opening
日期:	2022-09-28
上传时间:	2022-10-04 11:01:58 (UTC+8)
出版者:	國立中央大學
摘要:	分子中氟的存在通常會改變它們的生物物理和化學性質，例如疏水性、酸鹼性、反應性，這些性質使蛋白質和胜肽能有更多的應用。然而，製備氟化胺基酸的方法相當有限。本篇論文利用 L-阿拉伯糖衍生物噁唑烷酮稠合吖環丙烷來建立兩個掌性中心且有良好的立體選擇性，並利用氟離子進行開環反應得到氟化胺基酸的前驅物，再通過鄰二醇的氧化斷裂反應獲得氟化胺基酸。;The presence of fluorine within molecules often alters their biophysical and chemical properties, such as hydrophobicity, acidity/basicity and reactivity. It has been known that the incorporation of fluorines would broaden the applications of proteins and peptides. However, methods to prepare fluorinated amino acids are rather limited. Starting from L-arabinose, we developed a method to build chiral oxazolidinone-fused aziridines and their ring-open reactions by fluoride anion yielded highly functionalized organofluoride with good diastereoselective. Therefore, the fluorinated amino acids were prepared by oxidative cleavage of tetraols.
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