mt-tRNA COMPONENTS: SYNTHESIS OF (2-THIO)URIDINES MODIFIED WITH BLOCKED GLYCINE/TAURINE MOIETIES AT C-5,1

作者：Leszczynska Grazyna^*; Leonczak Piotr; Dziergowska Agnieszka; Malkiewicz Andrzej

来源：Nucleosides Nucleotides & Nucleic Acids, 2013, 32(11): 599-616.

DOI：10.1080/15257770.2013.838261

• Modified nucleosides
• reductive amination
• 5-formyluridine (f(5)U)
• 5-formyl-2-thiouridine (f(5)s(2)U)
• 5-carboxymethylaminomethyl(-2-thio)uridine (cmnm(5)(s(2))U)
• 5-taurinomethyl(-2-thio)uridine (m(5)(s(2))U)

In this paper, we discuss the usefulness of reductive amination of 5-formyl-2,3-O-isopropylidene(-2-thio)uridine with glycine or taurine esters in the presence of sodium triacetoxyborohydride (NaBH(OAc)(3)) for the synthesis of the native mitochondrial (mt) tRNA components 5-carboxymethylaminomethyl(-2-thio)uridine (cmnm(5)(s(2))U) and 5-taurinomethyl(-2-thio)uridine (m(5)(s(2))U) with a blocked amino acid function. 2-(Trimethylsilyl)ethyl and 2-(p-nitrophenyl)ethyl esters of glycine and 2-(2,4,5-trifluorophenyl)ethyl ester of taurine were selected as protection of carboxylic and sulfonic acid residues, respectively. The first synthesis of 5-formyl-2,3-O-isopropylidene-2-thiouridine is also reported.

• 出版日期2013-11-2