Synthesis of cyclohexyl carbocyclic puromycin and its inhibition of protein synthesis

Diastereoselectivity in the Epoxidation of Substituted Cyclohexenes by Dimethyldioxirane1,2

“…Separation of the products was accomplished by radial chromatography of the residue on a Chromatotron (silica gel plate), using acetone/CH 2 Cl 2 (5:95) as the eluent. The major product was identified as 3-benzamido- cis- 1,2-epoxycyclohexane ( cis -5g) by comparing its properties with those in the literature 24 and on the basis of the following data: colorless needles (CH 2 Cl 2 −hexane), mp 119−121 °C, lit . mp 116−117 °C; 1 H NMR (CDCl 3 ) δ 1.20−1.75 (m, 4H), 1.80−2.00 (m, 2H), 3.34 (s, 2H), 4.55−4.65 (m, 1H), 6.54 (br d, J = 7.82 Hz, 1H), 7.35−7.60 (m, 3H), 7.75−7.85 (m, 2H); 13 C NMR (CDCl 3 ) δ 18.47, 23.21, 26.37, 45.67, 54.14, 54.52, 126.86, 128.35, 131.33, 134.28, 166.70; MS (EI, 70 eV): m/z 217(M + , 1), 198(1), 146(15), 122(16), 105(100), 77(43), 67(2), 51(8); calcd for C 13 H 15 NO 2 : 217.27.…”

Synthesis and Antimicrobial Activity of 2′-Deoxypuromycin

“…The residue was dissolved in CHC13 , washed with sat. NaHC0 3 (10). A mixture of9 (620.7 mg, 1.57 mmol) and NaOMe (Na, 361mg, 15.7mmol) in MeOH (40ml) was stirred at room temperature for 20hr.…”

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

“…Although, for in vivo experiments, the 6-dimethylamino group is essential to escape the activity of adenosine deaminases, it is not needed for in vitro experiments on ribosomes as is the focus of this work. Several studies have shown that puromycin's dimethylamino group is not necessary for its biological activity. Experiments on the kinetics of the ribosomal peptidyl transfer reaction using our puromycin analogues are currently underway.…”