A model study directed towards the preparation of nucleopeptides via H-phosphonate intermediates.
The monofunctional phosphitylating reagents bis-(N,N-diethylamino)chlorophosphine and salicylchlorophosphine have been applied for the preparation of H-phosphonates of the amino acids serine, threonine and tyrosine. Experimental evidence showed that the latter reagent was less effective for the synthesis of a tyrosine H-phosphonate. The amino acids (peptide) H-phosphonates of serine or threonine proved to be suitable starting compounds for the formation of a phosphate diester bond with the 5'-OH of a d-nucleoside derivative using pivaloyl chloride as the activating reagent.
D007202:Indicators and Reagents; D009682:Magnetic Resonance Spectroscopy; D009698:Nucleoproteins / Q000138:chemical synthesis*; D063065:Organophosphonates; D010446:Peptide Fragments / Q000138:chemical synthesis*; D012694:Serine; D013329:Structure-Activity Relationship; D013912:Threonine; D014443:Tyrosine
D007202:Indicators and Reagents; D009698:Nucleoproteins; D063065:Organophosphonates; D010446:Peptide Fragments; D013912:Threonine; D014443:Tyrosine; D012694:Serine