Nucleotide Peptide Conjugate

2’-(3’)-O-(N-formyl)-aminoacyl-nucleoside-5’-phosphate

Method A: 5.5 mmol of CDI was added to the solution of 5 mmols of N-formyl-L or D-amino acid in 2 ml of DMF. The mixture was stirred for 15 min until the CO2 formation was stopped, and the solution obtained was added to 0.2 mmols of nucleotide (disodium salt) in 2 ml of water. The reaction mixture was stirred for 2.5 hr at room temperature and diluted with 80ml of cold acetone.

After centrifugation the solid residue was washed with cold acetone and dried in vacuo. The precipitate was dissolved in 1-2 ml of deionized water and applied to the silica gel column 25×1.5 cm. Elution was made with System 2 at 4^o , 30 ml / hr. The fractions containing formylamino acod esters of nucleotides were diluted with 2 volumes of ether, and the substances were extracted three times with 0.1 volume of water. The aqous solution was shaken with ether and freeze dried. The yields and certain characteristics of the obtained compound are presented in the original paper.

Method B: N-(N’-formyl)-aminoacyl-imidazole, prepared from 2 mmols of N-formylamino acid in 2 ml of DMF as described above, was added to the nucleotide solution in 3 ml of dry formamide. The reaction mixture was stirred overnight and then diluted with 50 ml of dry acetone and 50 ml of ether, the isolation of the compound was carried out analogously to method A.

Nucleic acid research Volume 4, Number 7, July 1977, 2233-