Chinese Journal of Organic Chemistry >
Rational Design and Synthesis of a Fluorinated Butyric Adenosine Derivative
Received date: 2013-11-05
Revised date: 2014-01-20
Online published: 2014-03-03
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), the key enzyme in the biosynthesis of the pantothenate acid, is considered to be a new target for anti-tuberculosis drug development. Based on the structure of the enzyme catalyzed reaction intermediate and bioisosterism principle, 5'-O-{[(R)-4-fluoro-2-hydroxy-3,3-dimethylbutanoyl]sulfamoyl}adenosine (1) was designed with the sulfamate isoster to replace the unstable phosphate moiety. The synthesis of this compound was achieved using pantolactone and adenosine as the starting materials through 9 steps of reaction. All the compounds were characterized by 1H NMR, 13C NMR and MS techniques.
Key words： adenosine derivative; pantothenate synthetase; anti-tuberculosis
Yao Houzong , Yin Wei , Chen Jinglei , Qiao Chunhua . Rational Design and Synthesis of a Fluorinated Butyric Adenosine Derivative[J]. Chinese Journal of Organic Chemistry, 2014 , 34(6) : 1222 -1226 . DOI: 10.6023/cjoc201311005
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