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. 2010 Nov 15;49(47):8885-8.
doi: 10.1002/anie.201001242.

The AlkB domain of mammalian ABH8 catalyzes hydroxylation of 5-methoxycarbonylmethyluridine at the wobble position of tRNA

Ye Fu  1 , Qing Dai, Wen Zhang, Jin Ren, Tao Pan, Chuan He
Affiliations

The AlkB domain of mammalian ABH8 catalyzes hydroxylation of 5-methoxycarbonylmethyluridine at the wobble position of tRNA

Ye Fu et al. Angew Chem Int Ed Engl. .
No abstract available

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Figures

Figure 1
Figure 1
Distinct domains and proposed function of ABH8. a) ABH8 contains three domains: the N-terminal RNA recognition motif (RRM; blue), the middle iron/αKG-dependent AlkB domain (red), and the C-terminal methyltransferase domain (green). The C-terminal domain is homologous to a tRNA modification methyltransferase Trm9 in yeast. b) The anticodon wobble-base U*34 in higher eukaryotes tRNAGly(U*CC) can be hypermodified. c) Examples of hypermodification on U*34: 5-carboxymethyluridine (cm5U), 5-methoxycarbonylmethyluridine (mcm5U), and 5-methoxycarbonylhydroxymethyluridine (mchm5U). d) The proposed sequential modification of the wobble U*34 in a 17-mer RNA that contains the anticodon stem–loop of tRNAGly(U*CC) by the two catalytic domains of ABH8.
Figure 2
Figure 2
Hydroxylation of mcm5U in a 17-mer tRNAGly(U*CC) anticodon stem-loop. a) The chemically synthesized 17-mer RNA oligonucleotide resembling the tRNAGly(U*CC) anticodon stem-loop was treated with mABH81−340 in the presence of iron(II) and α-KG. The HPLC traces show the appearance of a peak for the product (S)-mchm5U when mcm5U is converted in the presence of the enzyme. b) HRMS data of the product (S)-mchm5U confirms the addition of a hydroxy group to mcm5U. MES = 2-(N-morpholino)ethanesulfonic acid.
Scheme 1
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) (iPr2N)P(Cl)OCH2CH2CN, iPr2NEt, 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.
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