Functional lactide monomers: methodology and polymerization.
Side-chain-functionalized lactide analogues have been synthesized from commercially available amino acids and polymerized using stannous octoate as a catalyst. The synthetic strategy presented allows for the incorporation of any protected amino acid for the preparation of functionalized diastereomerically pure lactide monomers. The resulting functionalized cyclic monomers can be homopolymerized and copolymerized with lactides and then quantitatively deprotected forming new functional poly(lactide)-based materials. This strategy allows for the introduction of functional groups along a poly(lactide) (PLA) backbone that after deprotection can be viewed as chemical handles for further functionalization of PLA, yielding improved biomaterials for a variety of applications.
Gerhardt
Warren W
WW
School of Chemistry and Biochemistry and Woodruff School of Mechanical Engineering and Petit Institute for Bioengineering and Bioscience, Georgia Institute of Technology, Atlanta, Georgia 30332-0400, USA.
Noga
David E
DE
Hardcastle
Kenneth I
KI
García
Andrés J
AJ
Collard
David M
DM
Weck
Marcus
M
D000596:Amino Acids / Q000737:chemistry; D002208:Caproates / Q000737:chemistry; D002384:Catalysis; D018360:Crystallography, X-Ray; D019344:Lactic Acid / Q000031:analogs & derivatives / Q000138:chemical synthesis* / Q000737:chemistry; D008958:Models, Molecular; D015394:Molecular Structure; D013237:Stereoisomerism; D014001:Tin
D000596:Amino Acids; D002208:Caproates; D019344:Lactic Acid; C419565:2-ethylhexanoic acid tin(II) salt; D014001:Tin