title: Conversion of a primary amine to a labeled secondary amine by the addition of phenolic group and radioiodination.
abstract: To preserve the nucleophilicity of amino compounds during conjugative radioiodination, a new method for converting primary amines to phenolic secondary amines was developed. Amino acids were used as model compounds for establishing optimal conditions for the reductive amination. In the first step of the reaction, the aldehyde group of 4-hydroxybenzaldehyde (formylphenol) was reacted reversibly with an amino group to form an imine. The irreversible attachment of formylphenol to the amino group was accomplished by reduction of the imine with sodium cyanoborohydride. The pH optimum for the reaction was 5.0. Higher temperature has favorable effects on the rate and extent of the conjugation. Phenolic derivatives of amino compounds suitable for radioiodination are produced by the reactions described.
mesh_terms: D000588:Amines; D007457:Iodine Radioisotopes; D007553:Isotope Labeling / Q000379:methods*; D010636:Phenols; D013329:Structure-Activity Relationship
chemical_list: D000588:Amines; D007457:Iodine Radioisotopes; D010636:Phenols