Studies on transfer ribonucleic acids and related compounds. XXXII. Synthesis of ribonucleotides corresponding to residues 1-5 and 6-10 of tRNA^fMetfrom E.coli and their base conversion analogs

Abstract

E. Coli tRNAfMet fragments, C-G-C-G-Gp (bases 1-5), U-G-C-G-Gp (base 1 transition, analog) pG-G-C-G-Gp (base 1 transversion analog) and pG-G-s4U-G-Gp (bases 6-10) were synthesized by triester methods using 2'-O-(o-nitrobenzyl) nucleotides including a 3',5'-bisphosphorylated guanosine derivative. The s4U containing pentanucleotide was derived from the pG-G-C-G-Gp by treatment with liquid hydrogen sulfide.

Total synthesis of a RNA molecule with sequence identical to that of Escherichia coli formylmethionine tRNA.

“…Oligonucleotides corresponding to the rest ofthe molecule and certain oftheir analogs have been synthesized either by the. phosphodiester method (23,24) or by the triester method (25,26).In this paperwe report total synthesis ofa RNA molecule with a sequence identical to that of E. coli tRNAf~et obtained by the enzymatic joining of chemically synthesized fragments with RNA ligase. …”

“…Oligonucleotides corresponding to the rest ofthe molecule and certain oftheir analogs have been synthesized either by the. phosphodiester method (23,24) or by the triester method (25,26).…”

Solid‐Phase Supports for Oligonucleotide Synthesis

“…Cleavage of phosphoramidate linkages was used for the introduction of the 3 -terminal phosphates by two different methods. Anilidate protection of phosphorus removable by alkyl nitrites was extensively used in solutionphase oligonucleotide synthesis by the phosphotriester method (Ohtsuka et al, 1979). This strategy has been applied to preparation of oligonucleotide 3 -phosphates on a solid support 60, where benzidine was attached to a solid phase material (Fig.…”

Synthesis and properties of 5′-triphosphoryl 2′-5′ oligoadenylates (2-5A), and a general method for synthesis of 3′, 5′-bisphosphorylated oligonucleotides

“…NMR (CDC13): 6 (ppm), 4.30 (bs, 4H, 3',4',5'-CH);4.89 (d, 2H, Ar-CH2), 5.05 (bs, 1H, 2'-OH); 6.63 (d, 1H, 1'-CH), 8.50, 8.37 (s, 1H, 8-CH or 2-CH). 3'-0-(o-Nitrobenzyl)-N-benzoyladenosine 5'-phosphorodianilido-2'-(p-chlorophenyl) phosphate (10) 9 (730 mg, 1 mmol) was dissolved in pyridine (10 ml), dried by coevaporation of pyridine, and condensed with p-chlorophenyl phosphate (531 mg, 3 mmol) using DCC (1.5 g, 7.5 mmol) for 18 hr. Disappearance of 9 by TLC was confirmed and the mixture was treated with aqueous pyridine in the presence of n-hexane.…”

“…For a large scale preparation of 2-5A, we have employed the triester approach to prepare the 5'-phosphorylated trinucleotide (3b, n=2) using monomer units (7,8,10) as shown in Chart 2. The nucleotide (7) was reacted with the nucleoside (8) using mesitylenesulfonyl triazolide (MST) as the activating reagent to yield the dinucleoside monophosphate which was isolated after removal of the 5'-monomethoxytrityl group by chromatography on silica gel in a yield of 86%.…”