title: Solid-phase synthesis of polymers using the ring-opening metathesis polymerization.
abstract: We report a general method for the solid-phase synthesis of polymers via the ring-opening metathesis polymerization (ROMP). The method involves polymerization in solution to form a block copolymer, immobilization of the polymer via reaction of one block with a resin-bound functional group, modification of the other block, and liberation of the polymer from the resin. We demonstrated the utility of this approach by generating a block copolymer with an N-hydroxysuccinimidyl ester-substituted block (for on-resin functionalization) and a maleimide-substituted block (for conjugation to the resin). We showed that the Diels-Alder reaction can be employed to immobilize the polymers and that amines of diverse structure can be used to modify the resin-bound polymers. The reversibility of the furan-maleimide Diels-Alder adduct was exploited to liberate the polymer from the support. Specifically, treatment of the resin with cyclopentadiene resulted in complete polymer release. The resulting polymers are functional: they were as potent in assays with the lectin concanavalin A as polymers generated by traditional solution routes. We anticipate that this method can be used for the rapid synthesis of diverse polymers via ROMP.
authors.affiliation: Department of Chemistry, University of Wisconsin, Madison, Wisconsin 53706, USA.
authors.forename: Jason K
authors.initials: JK
authors.lastname: Pontrello
authors.forename: Matthew J
authors.initials: MJ
authors.lastname: Allen
authors.forename: Eric S
authors.initials: ES
authors.lastname: Underbakke
authors.forename: Laura L
authors.initials: LL
authors.lastname: Kiessling
mesh_terms: D004952:Esters / Q000737:chemistry; D007103:Immobilization; D015394:Molecular Structure; D011108:Polymers / Q000138:chemical synthesis*
chemical_list: D004952:Esters; D011108:Polymers