[NH2:1][C@H:2]([C:8]([OH:10])=[O:9])[CH2:3][CH2:4][CH2:5][CH2:6][NH2:7].[OH:11][P:12]([F:15])([OH:14])=[O:13].O.CO>C(O)C>[P:12]([F:15])([OH:14])([OH:13])=[O:11].[NH2:1][C@H:2]([C:8]([OH:10])=[O:9])[CH2:3][CH2:4][CH2:5][CH2:6][NH2:7]L-lysine monofluorophosphate was prepared by combining 29.2 grams of free-base lysine with 20 gm. (grams) of monofluorophosphoric acid in about 75 ml. of water. The resulting clear syrupy solution was poured into 750 ml. of a 50:50 mixture of methanol and ethanol (absolute) to precipitate the solid salt. The cake was collected after filtration and rinsed with methanol. The product (L-lysine monofluorophosphate) was then air dried. The L-lysine monofluorophosphate was tested in rat diets as described in Example I but at a level of 6.8 ppm fluoride. Caries reduction was 36%.
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