title: Studies toward the site specific incorporation of sugars into proteins: synthesis of glycosylated aminoacyl-tRNAs.
abstract: A series of glycosylated serine derivatives was synthesized from peracetylated sugars and Fmoc-protected serine; these were chemically esterified with the tris-(tetrabutylammonium) salt of pdCpA. The fully protected and deprotected glycosylated aminoacyl pdCpAs were ligated enzymatically to an abbreviated tRNA (tRNA-C(OH)) to provide the title compounds that are key intermediates in the elaboration of glycoproteins using readthrough of a nonsense codon.
authors.affiliation: Department of Chemistry, University of Virginia, Charlottesville 22901, USA.
authors.forename: N E
authors.initials: NE
authors.lastname: Fahmi
authors.forename: S
authors.initials: S
authors.lastname: Golovine
authors.forename: B
authors.initials: B
authors.lastname: Wang
authors.forename: S M
authors.initials: SM
authors.lastname: Hecht
mesh_terms: D018389:Codon, Nonsense; D003619:Dansyl Compounds / Q000494:pharmacology; D004586:Electrophoresis; D006023:Glycoproteins / Q000138:chemical synthesis*; D006031:Glycosylation; D006834:Hydrazines / Q000494:pharmacology; D009005:Monosaccharides / Q000378:metabolism; D014176:Protein Biosynthesis; D011130:RNA Ligase (ATP) / Q000378:metabolism; D012346:RNA, Transfer, Amino Acyl / Q000138:chemical synthesis* / Q000378:metabolism; D012694:Serine / Q000378:metabolism; D014158:Transcription, Genetic
chemical_list: D018389:Codon, Nonsense; D003619:Dansyl Compounds; D006023:Glycoproteins; D006834:Hydrazines; D009005:Monosaccharides; D012346:RNA, Transfer, Amino Acyl; C027913:dansyl hydrazine; D012694:Serine; D011130:RNA Ligase (ATP)