Synthesis of pCpCpA-3'-NH-phenylalanine as a ribosomal substrate
Program in Molecular Medicine; Graduate School of Biomedical Sciences; Department of Biochemistry and Molecular Biology
Life Sciences | Medicine and Health Sciences
[reaction: see text] The trinucleotide cytidylyl(3'-->5'phosphoryl)cytidylyl(3'-->5'phosphoryl)-3'-deoxy-3'-(L-ph enylalanyl) amido adenosine (CpCpA-NH-Phe) was synthesized by phosphoramidite chemistry from 3'-amino-3'-deoxyadenosine as the ribosomal substrate. The 3'-amino-3'-deoxyadenosine was first converted to 3'-(N-tert-butyloxycarbonyl-L-phenylalanine)amido-3'-deoxy-6-N,6-N,2'-O-tr ibenzoyl-adenosine and then coupled with cytidine phosphoramidite to produce the fully protected CpCpA-NH-Phe-Boc. The title product was obtained after removing all protection groups and then radiolabeled with (32)P to yield pCpCpA-NH-Phe, which demonstrated high activity for the peptidyl transferase reaction in the ribosome.
DOI of Published Version
Org Lett. 2002 Oct 17;4(21):3615-8.
Zhang B, Zhang L, Sun L, Cui Z. (2002). Synthesis of pCpCpA-3'-NH-phenylalanine as a ribosomal substrate. GSBS Student Publications. https://doi.org/10.1021/ol026560f. Retrieved from https://escholarship.umassmed.edu/gsbs_sp/721