title: Synthesis of an mRNA fragment of alanyl-tRNA synthetase gene in Escherichia coli using the 6-methyl-3-pyridyl group for protection of the imide functions of uridine and guanosine.
abstract: The synthesis of 5'-GpGpUpGpU-3' is reported to demonstrate the synthetic use of the 6-methyl-3-pyridyl group for the protection of the O-4 and O-6 imide functions of uridine and guanosine, respectively. The 2'- and 5'-hydroxyl functions of the key intermediates were protected with two acid-labile groups: 3-methoxy-1,5-dicarbomethoxypentane-3-yl (MDMP) and 9-(4-octadecyloxyphenyl)xanthen-9-yl (C18Px), respectively. The internucleotide phosphotriesters were protected with 2-chlorophenyl and the 9-fluorenylmethyl group was employed for 3'-terminal phosphate protection.
mesh_terms: D000412:Alanine-tRNA Ligase / Q000235:genetics*; D000604:Amino Acyl-tRNA Synthetases / Q000235:genetics*; D055598:Chemical Phenomena; D002627:Chemistry, Physical; D002851:Chromatography, High Pressure Liquid; D004926:Escherichia coli / Q000201:enzymology* / Q000235:genetics; D005813:Genes, Synthetic; D006151:Guanosine / Q000378:metabolism; D012329:RNA, Bacterial / Q000096:biosynthesis* / Q000235:genetics; D012333:RNA, Messenger / Q000096:biosynthesis* / Q000235:genetics; D014529:Uridine / Q000378:metabolism
chemical_list: D012329:RNA, Bacterial; D012333:RNA, Messenger; D006151:Guanosine; D000604:Amino Acyl-tRNA Synthetases; D000412:Alanine-tRNA Ligase; D014529:Uridine