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
Medical Subject Headings
Molecular Structure; Phenylalanine; Ribosomes
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.
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Citation: Org Lett. 2002 Oct 17;4(21):3615-8.
Zhang, Biliang; Zhang, Lei; Sun, Lele; and Cui, Zhiyong, "Synthesis of pCpCpA-3'-NH-phenylalanine as a ribosomal substrate" (2002). GSBS Student Publications. 721.