title: Dynamic polythioesters via ring-opening polymerization of 1,4-thiazine-2,5-diones.
abstract: We describe the preparation and characterization of polythioesters composed of alternating alpha-amino acid and alpha-thioglycolic acid residues that undergo dynamic constitutional exchange under mild conditions. The polymers are assembled via reversible ring-opening polymerizations of 1,4-thiazine-2,5-diones and related monomers in solution-phase conditions that do not require the use of transition metal catalysts. Because 1,4-thiazine-2,5-diones can be derived in part from alpha-amino acids, a variety of side chain functionalized monomers in optically pure forms could readily be accessed. In addition, the resulting polythioesters have the potential for intra- and inter-chain hydrogen bonding, which is known to impart materials properties to other previously studied polyamides. The studies reported here could be useful in advancing a new class of biodegradable polymers and furthermore suggest that dynamic constitutional exchange could be exploited to modify many known synthetic and natural polythioesters.
authors: Department of Chemistry, The Scripps Research Institute, 10550 North Torrey Pines Road, La Jolla, CA 92037, USA.
authors: Yasuyuki
authors: Y
authors: Ura
authors: Mohammad
authors: M
authors: Al-Sayah
authors: Javier
authors: J
authors: Montenegro
authors: John M
authors: JM
authors: Beierle
authors: Luke J
authors: LJ
authors: Leman
authors: M Reza
authors: MR
authors: Ghadiri
mesh_terms: D004952:Esters / Q000737:chemistry*; D011108:Polymers / Q000138:chemical synthesis / Q000737:chemistry*; D013843:Thiazines / Q000737:chemistry*
chemical_list: D004952:Esters; D011108:Polymers; D013843:Thiazines