The synthesis and characterization of N-sulfo-2-amino tricarballylate: an analog of phosphocitrate and inhibitor of calcification.

The synthesis of N-sulfo-2-amino tricarballylate, a sulfamate analog of phosphocitrate, is described using pyridine-sulfur trioxide to sulfonate 2-amino tricarballylate. The product was purified using selective precipitation and chromatographic techniques and characterized by a variety of physical and chemical means. In particular, its ability to inhibit hydroxyapatite formation and calcium oxalate crystallization was assessed by comparison with known inhibitors including phosphocitrate and pyrophosphate. On the basis of these results, this new compound may ultimately have a role in preventing abnormal biological calcification.