Studies toward the site specific incorporation of sugars into proteins: synthesis of glycosylated aminoacyl-tRNAs.
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.
Fahmi
N E
NE
Department of Chemistry, University of Virginia, Charlottesville 22901, USA.
Golovine
S
S
Wang
B
B
Hecht
S M
SM
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
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)