Synthesis, decomposition, and vasodilator action of some new S-nitrosated dipeptides

A number of amino acid methyl esters have been coupled to N-acetylpenicillamine to give a range of sulfur-containing dipeptides. These have been nitrosated to give a family of structurally related NO-donor drugs. The catalytic effect of copper ions upon the release of NO from these compounds is much less than that upon S-nitroso-N-acetylpenicillamine. However, all the nitrosated dipeptides respond in a similar way with little variation in the value of kCu. On the other hand, the vasodilator action of these compounds and the inhibiting effect of hemoglobin do vary quite considerably within the family. It is suggested that this indicates some tissue penetration by these drugs.