Design of new photoaffinity labels for ribosomal peptidyltransferase. 1978

K Quiggle, and M L Wejrowski, and S Chládek

The chemical syntheses of 6-azido-2'(3')-O-L-phenylalanylpurine ribonucleoside (4a), 2'(3')-O-(4-azido-L-phenylalanyl)adenosine (4b), and cytidylyl(3' leads to 5')-6-azido-2'(3')-O-L-phenylalanylpurine ribonucleoside (7) are described. 6-Azidopurine ribonucleoside 5'-triphosphate (10) was also synthesized starting from 6-methylmercaptopurine ribonucleoside. All of these compounds (4a, 4b, 7, and 10) are readily photolyzed by ultraviolet (UV) light. Compounds 4a, 4b, and 7 are active in the ribosomal peptidyltransferase-catalyzed release of the Ac-Phe residue from the Ac-Phe-tRNA-70S ribosome-poly(U) complex. It follows that the 6-azidopurine moiety of compounds 4a and 7, as well as the 4-azido-L-phenylalanine moiety of 4b, are recognized by the peptidyltransferase enzyme, and therefore these moieties are suggested for incorporation into tRNA as photoaffinity labeling reagents.

UI MeSH Term Description Entries
D007700 Kinetics The rate dynamics in chemical or physical systems.
D008722 Methods A series of steps taken in order to conduct research. Techniques,Methodological Studies,Methodological Study,Procedures,Studies, Methodological,Study, Methodological,Method,Procedure,Technique
D009682 Magnetic Resonance Spectroscopy Spectroscopic method of measuring the magnetic moment of elementary particles such as atomic nuclei, protons or electrons. It is employed in clinical applications such as NMR Tomography (MAGNETIC RESONANCE IMAGING). In Vivo NMR Spectroscopy,MR Spectroscopy,Magnetic Resonance,NMR Spectroscopy,NMR Spectroscopy, In Vivo,Nuclear Magnetic Resonance,Spectroscopy, Magnetic Resonance,Spectroscopy, NMR,Spectroscopy, Nuclear Magnetic Resonance,Magnetic Resonance Spectroscopies,Magnetic Resonance, Nuclear,NMR Spectroscopies,Resonance Spectroscopy, Magnetic,Resonance, Magnetic,Resonance, Nuclear Magnetic,Spectroscopies, NMR,Spectroscopy, MR
D010458 Peptidyl Transferases Acyltransferases that use AMINO ACYL TRNA as the amino acid donor in formation of a peptide bond. There are ribosomal and non-ribosomal peptidyltransferases. Peptidyl Transferase,Peptidyl Translocase,Peptidyl Translocases,Peptidyltransferase,Transpeptidase,Transpeptidases,Peptidyltransferases,Transferase, Peptidyl,Transferases, Peptidyl,Translocase, Peptidyl,Translocases, Peptidyl
D010782 Photolysis Chemical bond cleavage reactions resulting from absorption of radiant energy. Photodegradation
D011684 Purine Nucleosides Purines with a RIBOSE attached that can be phosphorylated to PURINE NUCLEOTIDES. Purine Nucleoside,Nucleoside, Purine,Nucleosides, Purine
D000217 Acyltransferases Enzymes from the transferase class that catalyze the transfer of acyl groups from donor to acceptor, forming either esters or amides. (From Enzyme Nomenclature 1992) EC 2.3. Acyltransferase
D000345 Affinity Labels Analogs of those substrates or compounds which bind naturally at the active sites of proteins, enzymes, antibodies, steroids, or physiological receptors. These analogs form a stable covalent bond at the binding site, thereby acting as inhibitors of the proteins or steroids. Affinity Labeling Reagents,Labeling Reagents, Affinity,Labels, Affinity,Reagents, Affinity Labeling
D012270 Ribosomes Multicomponent ribonucleoprotein structures found in the CYTOPLASM of all cells, and in MITOCHONDRIA, and PLASTIDS. They function in PROTEIN BIOSYNTHESIS via GENETIC TRANSLATION. Ribosome
D013056 Spectrophotometry, Ultraviolet Determination of the spectra of ultraviolet absorption by specific molecules in gases or liquids, for example Cl2, SO2, NO2, CS2, ozone, mercury vapor, and various unsaturated compounds. (McGraw-Hill Dictionary of Scientific and Technical Terms, 4th ed) Ultraviolet Spectrophotometry

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