Antibiotic-bound poly(caprolactone) polymer
This invention is the design and synthesis of a caprolactone monomer which bears a pendant protected carboxyl group. This monomer has been copolymerized with caprolactone in varying ratios. After polymerization, the protecting group can be removed and an antibiotic can be attached as a new pendant group. The bioactivity of the antibiotic-bound poly(caprolactone) polymer is described.
1. A compound consisting of:
a caprolactone ring;
a spacer consisting of a methylene group, and a carbonyl group at a terminus of the methylene group, wherein the methylene group at the other terminus is attached to the C-4 position on the caprolactone ring; and
a 2-azetidinone, wherein an alkylthio is attached to the N-1 position, a hydroxyl group is attached to the C-3 position and an aryl ring is attached to the C-4 position, the C-3 hydroxyl group is joined to the spacer by removing the hydrogen atom of the hydroxyl group.
2. The compound represented by the formula:
3. The compound represented by the formula:
4. The compound represented by the formula:
5. A method of producing a compound comprising:
providing
a caprolactone ring;
a spacer, consisting of one methylene group, and a carbonyloxy group at one terminus of the methylene groups, wherein the methylene group at the other terminus is attached to the C-4 position of the caprolactone ring;
a protecting group, attached to the carbonyloxy group on the spacer;
a 2-azetidinone, wherein an alkylthio is attached to the N-1 position, a hydroxyl group is attached to the C-3 position and an aryl ring is attached to the C-4 position;
removing the protecting group from the spacer attached to the caprolactone;
forming an ester between the hydroxyl group on the 2-azetidinone and the carbonyloxy group on the spacer attached to the caprolactone.
6. The method of claim 5 wherein the protecting group is selected from the group consisting of a benzyl and a tert-butyl.