Rational Design and Synthesis of a Fluorinated Adenosine Derivative

doi:10.6023/cjoc201212001

Chin. J. Org. Chem. ›› 2013, Vol. 33 ›› Issue (07): 1578-1582.DOI: 10.6023/cjoc201212001 Previous Articles Next Articles

Notes

一种氟代腺苷类衍生物的合理设计与合成

许芝祥, 尹伟, 陈晶磊, 乔春华

苏州大学药学院苏州 215123

收稿日期:2012-12-01 修回日期:2013-01-26 发布日期:2013-02-05
通讯作者: 乔春华 E-mail:qiaochunhua@suda.edu.cn
基金资助:
国家自然科学基金(No. 81072514)和国家自然青年科学基金(No. 21002067)资助项目

Rational Design and Synthesis of a Fluorinated Adenosine Derivative

Xu Zhixiang, Yin Wei, Chen Jinglei, Qiao Chunhua

College of Pharmacy, Soochow University, Suzhou 215123

Received:2012-12-01 Revised:2013-01-26 Published:2013-02-05
Supported by:
Project supported by the National Natural Science Foundation of China (No. 81072514) and the National Natural Science Foundation for Young Scientists of China (No. 21002067).

Pantothenate synthetase (PS), a member of adenosine acylation enzyme family, was the new target of anti-tuberculosis drug development. Employing bioisostere principle, 5'-O-{[(R)-2-hydroxy-3,3-dimethylbutanoyl]sulfamoyl}-2'-deoxy-2'-fluoroadenosine (1), a mimic of the PS catalyzed reaction intermediate, was rational designed by substituting the 2'-hydroxyl group of intermediate sugar ring with fluorine. This compound was synthesized using D-tertiary leucine and vidarabine as the starting materials by 9 steps of reaction, and its structure was fully characterized by ¹H NMR, ¹³C NMR and HR-MS techniques.

Key words: fluorinated adenosine derivative, pantothenate synthetase, anti-tuberculosis, total synthesis

Cite this article

Xu Zhixiang, Yin Wei, Chen Jinglei, Qiao Chunhua. Rational Design and Synthesis of a Fluorinated Adenosine Derivative[J]. Chin. J. Org. Chem., 2013, 33(07): 1578-1582.

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一种氟代腺苷类衍生物的合理设计与合成

Rational Design and Synthesis of a Fluorinated Adenosine Derivative

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