A Practical Route to 3‘-Amino-3‘-deoxyadenosine Derivatives and Puromycin Analogues

3‘-Aminoacylamino-3‘-deoxyadenosines, analogues of the antibiotic puromycin, have been synthesized from adenosine. They key 3‘-azido derivative 10 was obtained through a 3‘-oxidation/reduction/substitution procedure. A modified purification protocol on a larger scale was developed for the oxidation...

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Bibliographic Details
Published in:Journal of organic chemistry 2003-03, Vol.68 (5), p.2038-2041
Main Authors: Nguyen-Trung, Nhat Quang, Botta, Oliver, Terenzi, Silvia, Strazewski, Peter
Format: Article
Language:English
Subjects:
Adenosine
Carbohydrates. Nucleosides and nucleotides
Chemistry
Chemistry, Organic - methods
Deoxyadenosines - analysis
Deoxyadenosines - chemical synthesis
Exact sciences and technology
Indicators and Reagents
Magnetic Resonance Spectroscopy
Molecular Structure
Nucleosides, nucleotides and oligonucleotides
Organic chemistry
Preparations and properties
Puromycin - analogs & derivatives
Puromycin - analysis
Puromycin - chemical synthesis
Stereoisomerism
Structure-Activity Relationship
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Summary:3‘-Aminoacylamino-3‘-deoxyadenosines, analogues of the antibiotic puromycin, have been synthesized from adenosine. They key 3‘-azido derivative 10 was obtained through a 3‘-oxidation/reduction/substitution procedure. A modified purification protocol on a larger scale was developed for the oxidation step using the Garegg reagent. The coupling reaction between an Fmoc-l-amino acid and the fully protected form of 3‘-amino-3‘-deoxyadenosine 11 furnished the aminoacylated compounds 12 in high yields. The puromycin analogues were obtained in 10 steps and up to 23% (14c) overall yield.
ISSN:0022-3263
1520-6904
DOI:10.1021/jo026627c