title: Synthesis of pdCpAs and transfer RNAs activated with thiothreonine and derivatives.
abstract: N,S-diprotected L-thiothreonine and L-allo-thiothreonine derivatives were synthesized using a novel chemical strategy, and used for esterification of the dinucleotide pdCpA. The aminoacylated dinucleotides were then employed for the preparation of activated suppressor tRNA(CUA) transcripts. Thiothreonine and allo-thiothreonine were incorporated into a predetermined position of a catalytically competent dihydrofolate reductase (DHFR) analogue lacking cysteine, and the elaborated proteins were derivatized site-specifically at the thiothreonine residue with a fluorophore.
authors.affiliation: Center for BioEnergetics, Biodesign Institute, and Department of Chemistry and Biochemistry, Arizona State University, Tempe, AZ 85287, USA.
authors.forename: Shengxi
authors.initials: S
authors.lastname: Chen
authors.forename: Nour Eddine
authors.initials: NE
authors.lastname: Fahmi
authors.forename: Ryan C
authors.initials: RC
authors.lastname: Nangreave
authors.forename: Youcef
authors.initials: Y
authors.lastname: Mehellou
authors.forename: Sidney M
authors.initials: SM
authors.lastname: Hecht
mesh_terms: D015226:Dinucleoside Phosphates / Q000138:chemical synthesis* / Q000737:chemistry / Q000378:metabolism*; D015394:Molecular Structure; D012343:RNA, Transfer / Q000737:chemistry / Q000378:metabolism*; D013237:Stereoisomerism; D013912:Threonine / Q000031:analogs & derivatives* / Q000737:chemistry*; D046249:Transfer RNA Aminoacylation
chemical_list: D015226:Dinucleoside Phosphates; C062195:5'-phospho-2'-deoxyribocytidylylriboadenosine; D013912:Threonine; D012343:RNA, Transfer