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Chinese Journal of Organic Chemistry >

2013 , Vol. 33 >Issue 07: 1578 - 1582

DOI: https://doi.org/10.6023/cjoc201212001

Notes

Rational Design and Synthesis of a Fluorinated Adenosine Derivative

  • Xu Zhixiang ,
  • Yin Wei ,
  • Chen Jinglei ,
  • Qiao Chunhua
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  • College of Pharmacy, Soochow University, Suzhou 215123

Received date: 2012-12-01

  Revised date: 2013-01-26

  Online 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).

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Abstract

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]. Chinese Journal of Organic Chemistry, 2013 , 33(07) : 1578 -1582 . DOI: 10.6023/cjoc201212001

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