Abstract
The phage-inactivating activity of L-ascorbic acid (AsA) is well known. To examine the structure-activity relationship of AsA, 13 derivatives substituted at C2, C3, C5 or C6 of AsA were synthesized and tested for phage-inactivating activity against 9 phages. C2- and C2,6-substituted derivatives, in general, had the same activity as ASA or lower activity than AsA. C6- and C5,6-substituted ones had the same activity as AsA. C3- and C2,3-substituted ones had no activity. The results obtained show that the phage-inactivating activity of ASA is due to the enediol system and the hydroxyl group at C3 in the enediol system is necessary for the activity. Another purpose of this study is to find ASA derivatives with higher activity than AsA. 2-O-octanoyl-AsA exhibited about 3 times higher activity on phage MS2 and 2,6-di-O-benzoyl-AsA did about 10 times higher activity on phage T5.
