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 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.
Nguyen-Trung
Nhat Quang
NQ
Institute of Organic Chemistry, University of Basel, St. Johanns-Ring 19, CH-4056 Basel, Switzerland.
Botta
Oliver
O
Terenzi
Silvia
S
Strazewski
Peter
P
D000241:Adenosine; D002625:Chemistry, Organic / Q000379:methods; D003839:Deoxyadenosines / Q000032:analysis / Q000138:chemical synthesis*; D007202:Indicators and Reagents; D009682:Magnetic Resonance Spectroscopy; D015394:Molecular Structure; D011691:Puromycin / Q000031:analogs & derivatives* / Q000032:analysis / Q000138:chemical synthesis*; D013237:Stereoisomerism; D013329:Structure-Activity Relationship
D003839:Deoxyadenosines; D007202:Indicators and Reagents; C019247:3'-amino-3'-deoxyadenosine; D011691:Puromycin; D000241:Adenosine