Synthesis of novel mRNA 5' cap-analogues: dinucleoside P1, P3-tri-, P1, P4-tetra-, and P1, P5-pentaphosphates.
A series of new mRNA anti reverse cap analogues (ARCA) was designed to obtain a tool for studying the mechanism of protein translation. Dinucleoside P1, P3-tri-, P1, P4-tetra- and P1, P5-pentaphosphates, linked by a 5'-to-5' phosphate bridge and composed of modified 7-methylguanosine and guanosine, have been synthesized. The hydroxyl group (2'OH or 3'OH) in 7-metylguanosine moiety was replaced by -OCH3 or -H in order to obtain the cap analogues capable to be correctly incorporated into synthetic mRNA transcripts. Tri-, tetra-, and pentaphosphates were prepared by ZnCl2 catalyzed condensation in DMF of derivatives of the 7-methylguanosine diphosphates with the guanosine mono-, di- and triphosphate P-imidazolides, respectively. The structures of the novel compounds were established by means of 1H and 31P NMR spectra.
Jemielity
Jacek
J
Department of Biophysics, Institute of Experimental Physics, Warsaw University, Warsaw, Poland.
Stepinski
Janusz
J
Jaremko
Magdalena
M
Haber
Dorota
D
Stolarski
Ryszard
R
Rhoads
Robert E
RE
Darzynkiewicz
Edward
E
D015226:Dinucleoside Phosphates / Q000138:chemical synthesis*; D015195:Drug Design; D007202:Indicators and Reagents; D008968:Molecular Conformation; D014176:Protein Biosynthesis; D012315:RNA Caps / Q000138:chemical synthesis*; D012333:RNA, Messenger / Q000138:chemical synthesis
D015226:Dinucleoside Phosphates; D007202:Indicators and Reagents; D012315:RNA Caps; D012333:RNA, Messenger