TY - JOUR
T1 - Modified aminoacyl-tRNA. III. A general procedure for the synthesis of dipeptidyl transfer RNA
AU - Lapidot, Y.
AU - de Groot, N.
AU - Rappoport, S.
AU - Hamburger, A. D.
PY - 1967/12/19
Y1 - 1967/12/19
N2 - A general method for the preparation of dipeptidyl transport RNA (tRNA) is described. The synthesis involves a reaction between N-hydroxysuccinimide esters of N-monomethoxytritylamino acids and aminoacyl-tRNA. The activated N-protected amino acids react specifically with the amino group of the amino acid attached to the tRNA and do not react with any of the functional groups of the tRNA. [14C]Valyl-, [14C]phenylalanyl- and [14C]methionyl-tRNA could be 100 % transformed into the corresponding dipeptidyl-tRNA when they were reacted with activated, N-protected glycine and alanine. With the activated N-protected phenylalanine only 80-85 % of dipeptidyl-tRNA was formed. Mono-p-methoxytrityl, notwithstanding its bulkiness12, was found suitable for protecting the amino group of several amino acids. In all the reactions tested, the monomethoxytrityl remained attached to the amino group during the acylation and could be removed from the dipeptidyl-tRNA under mild acidic conditions. The tRNA of the dipeptidyl-tRNA did not lose its biological properties as a result of the chemical synthesis. Dipeptidyl-tRNA could be bound to ribosomes in a polyuridylic acid dependent reaction, and the tRNA could also be recharged with amino acid after removal of the dipeptide from the tRNA by mild alkaline hydrolysis.
AB - A general method for the preparation of dipeptidyl transport RNA (tRNA) is described. The synthesis involves a reaction between N-hydroxysuccinimide esters of N-monomethoxytritylamino acids and aminoacyl-tRNA. The activated N-protected amino acids react specifically with the amino group of the amino acid attached to the tRNA and do not react with any of the functional groups of the tRNA. [14C]Valyl-, [14C]phenylalanyl- and [14C]methionyl-tRNA could be 100 % transformed into the corresponding dipeptidyl-tRNA when they were reacted with activated, N-protected glycine and alanine. With the activated N-protected phenylalanine only 80-85 % of dipeptidyl-tRNA was formed. Mono-p-methoxytrityl, notwithstanding its bulkiness12, was found suitable for protecting the amino group of several amino acids. In all the reactions tested, the monomethoxytrityl remained attached to the amino group during the acylation and could be removed from the dipeptidyl-tRNA under mild acidic conditions. The tRNA of the dipeptidyl-tRNA did not lose its biological properties as a result of the chemical synthesis. Dipeptidyl-tRNA could be bound to ribosomes in a polyuridylic acid dependent reaction, and the tRNA could also be recharged with amino acid after removal of the dipeptide from the tRNA by mild alkaline hydrolysis.
UR - http://www.scopus.com/inward/record.url?scp=0014211207&partnerID=8YFLogxK
U2 - 10.1016/0005-2787(67)90181-5
DO - 10.1016/0005-2787(67)90181-5
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C2 - 6081519
AN - SCOPUS:0014211207
SN - 0005-2787
VL - 149
SP - 532
EP - 539
JO - BBA Section Nucleic Acids And Protein Synthesis
JF - BBA Section Nucleic Acids And Protein Synthesis
IS - 2
ER -