Synthesis of a 3-methyluridine phosphoramidite to investigate the role of methylation in a ribosomal RNA hairpin.
The synthesis of a 5'-O-BzH-2'-O-ACE-protected-3-methyluridine phosphoramidite is reported [BzH, benzhydryloxy-bis(trimethylsilyloxy)silyl; ACE, bis(2-acetoxyethoxy)methyl]. The phosphoramidite was employed in solid-phase RNA synthesis to generate a series of RNA hairpins containing single or multiple modifications, including the common nucleoside pseudouridine. Three 19-nucleotide hairpin RNAs that represent the 1920-loop region (G(1906)-C(1924)) of Escherichia coli 23S ribosomal RNA were generated. Modifications were present at positions 1911, 1915, and 1917. The stabilities and structures of the three RNAs were examined by using thermal melting, circular dichroism, and NMR spectroscopy
Chui
Helen M P
HM
Department of Chemistry, Wayne State University, Detroit, MI 48202, USA.
Meroueh
May
M
Scaringe
Stephen A
SA
Chow
Christine S
CS
D002942:Circular Dichroism; D009682:Magnetic Resonance Spectroscopy; D008745:Methylation; D009690:Nucleic Acid Conformation; D009943:Organophosphorus Compounds / Q000138:chemical synthesis* / Q000737:chemistry; D012335:RNA, Ribosomal / Q000737:chemistry* / Q000378:metabolism*; D012338:RNA, Ribosomal, 23S / Q000737:chemistry / Q000378:metabolism; D014529:Uridine / Q000031:analogs & derivatives* / Q000138:chemical synthesis* / Q000737:chemistry
C453000:3-methyluridine phosphoramidite; D009943:Organophosphorus Compounds; D012335:RNA, Ribosomal; D012338:RNA, Ribosomal, 23S; C008513:3-methyluridine; D014529:Uridine