The AlkB domain of mammalian ABH8 catalyzes hydroxylation of 5-methoxycarbonylmethyluridine at the wobble position of tRNA - PubMed (original) (raw)

Scheme 1

Synthesis of mcm5U phosphoramidite (5), and incorporation of mcm5U and cm5U into a tRNAGly(U*CC) anticodon stem–loop oligomer sequence (RNA-I and RNA-II). Reaction conditions: a) Ac2O, Py, RT, overnight; b) BzCl, DMAP, NEt3, 0.5 h; c) CH2(COMe)2, DBU, THF, RT, overnight; d) NaOMe, MeOH, 50°C, 1 h; e) DMTr, Py, RT, overnight; f) TBDMSCl, Im, Py, RT, 10 h; g) (_i_Pr2N)P(Cl)OCH2CH2CN, _i_Pr2NEt, THF, RT, 4 h; h) standard solid-phase RNA synthesis and subsequent deprotection under ultramild conditions (see the Supporting Information). Bz=benzoyl, DBU=1,8-diazabicyclo[5.4.0]undec-7-ene, DMAP=4-dimethylaminopyridine, Im=imidazole, Py=pyridine, TBDMS=_tert_-butyldimethylsilyl, THF=tetrahydrofuran.