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Synthesis of well-defined graft copolymers by combination of enzymatic polycondensation and "click" chemistry.
Biomacromolecules 2010; 11(12):3660-7B

Abstract

Aliphatic polyesters having pendant azide groups were prepared by enzymatic polycondensation in the presence of lipase from Candida antarctica type B (CAL-B). The grafting reaction to the N(3)-functional polyester was carried out quantitatively at room temperature using copper-catalyzed azide-alkyne cycloaddition (CuAAC, "click" reaction) with monoalkyne-functional poly(ethylene oxide) (alkyne-PEO, M(n) = 750 g/mol). Furthermore, both enzymatic polycondensation and "click" reaction were carried out successfully in sequential one-pot reaction. The graft copolymer was surface-active and self-assembled in water. The graft copolymer had a critical aggregation concentration (cac) of 3 × 10(-2) μM in water determined by surface tension measurements. Above cac, the graft copolymer formed single chains and aggregates having a hydrodynamic radius of ∼75 nm. Furthermore, the surface activity of the polymers at the air-water interface was studied by Langmuir trough measurements. The Langmuir isotherm of the graft polymer showed a pseudoplateau resulting from desorption of PEO chains into the subphase upon compression.

Authors+Show Affiliations

Martin Luther University Halle-Wittenberg, Department of Chemistry, D-06099 Halle (Saale), Germany.No affiliation info availableNo affiliation info available

Pub Type(s)

Journal Article
Research Support, Non-U.S. Gov't

Language

eng

PubMed ID

21086994

Citation

Naolou, Toufik, et al. "Synthesis of Well-defined Graft Copolymers By Combination of Enzymatic Polycondensation and "click" Chemistry." Biomacromolecules, vol. 11, no. 12, 2010, pp. 3660-7.
Naolou T, Busse K, Kressler J. Synthesis of well-defined graft copolymers by combination of enzymatic polycondensation and "click" chemistry. Biomacromolecules. 2010;11(12):3660-7.
Naolou, T., Busse, K., & Kressler, J. (2010). Synthesis of well-defined graft copolymers by combination of enzymatic polycondensation and "click" chemistry. Biomacromolecules, 11(12), pp. 3660-7. doi:10.1021/bm1011085.
Naolou T, Busse K, Kressler J. Synthesis of Well-defined Graft Copolymers By Combination of Enzymatic Polycondensation and "click" Chemistry. Biomacromolecules. 2010 Dec 13;11(12):3660-7. PubMed PMID: 21086994.
* Article titles in AMA citation format should be in sentence-case
TY - JOUR T1 - Synthesis of well-defined graft copolymers by combination of enzymatic polycondensation and "click" chemistry. AU - Naolou,Toufik, AU - Busse,Karsten, AU - Kressler,Jörg, Y1 - 2010/11/18/ PY - 2010/11/20/entrez PY - 2010/11/23/pubmed PY - 2011/4/13/medline SP - 3660 EP - 7 JF - Biomacromolecules JO - Biomacromolecules VL - 11 IS - 12 N2 - Aliphatic polyesters having pendant azide groups were prepared by enzymatic polycondensation in the presence of lipase from Candida antarctica type B (CAL-B). The grafting reaction to the N(3)-functional polyester was carried out quantitatively at room temperature using copper-catalyzed azide-alkyne cycloaddition (CuAAC, "click" reaction) with monoalkyne-functional poly(ethylene oxide) (alkyne-PEO, M(n) = 750 g/mol). Furthermore, both enzymatic polycondensation and "click" reaction were carried out successfully in sequential one-pot reaction. The graft copolymer was surface-active and self-assembled in water. The graft copolymer had a critical aggregation concentration (cac) of 3 × 10(-2) μM in water determined by surface tension measurements. Above cac, the graft copolymer formed single chains and aggregates having a hydrodynamic radius of ∼75 nm. Furthermore, the surface activity of the polymers at the air-water interface was studied by Langmuir trough measurements. The Langmuir isotherm of the graft polymer showed a pseudoplateau resulting from desorption of PEO chains into the subphase upon compression. SN - 1526-4602 UR - https://www.unboundmedicine.com/medline/citation/21086994/Synthesis_of_well_defined_graft_copolymers_by_combination_of_enzymatic_polycondensation_and_"click"_chemistry_ L2 - https://dx.doi.org/10.1021/bm1011085 DB - PRIME DP - Unbound Medicine ER -