title: mt-tRNA components: synthesis of (2-thio)uridines modified with blocked glycine/taurine moieties at C-5,1.
abstract: 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 (τm(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.
authors.affiliation: a Institute of Organic Chemistry , Lodz University of Technology , Lodz , Poland.
authors.forename: Grazyna
authors.initials: G
authors.lastname: Leszczynska
authors.forename: Piotr
authors.initials: P
authors.lastname: Leonczak
authors.forename: Agnieszka
authors.initials: A
authors.lastname: Dziergowska
authors.forename: Andrzej
authors.initials: A
authors.lastname: Malkiewicz
mesh_terms: D005998:Glycine / Q000378:metabolism*; D007202:Indicators and Reagents; D008928:Mitochondria / Q000378:metabolism*; D012343:RNA, Transfer / Q000378:metabolism*; D013654:Taurine / Q000378:metabolism*; D013891:Thiouridine / Q000031:analogs & derivatives* / Q000737:chemistry / Q000378:metabolism
chemical_list: C105273:2-thiouridine; D007202:Indicators and Reagents; D013891:Thiouridine; D013654:Taurine; D012343:RNA, Transfer; D005998:Glycine