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Lipase-catalyzed synthesis of poly(amine-co-esters) via copolymerization of diester with amino-substituted diol.
Biomacromolecules 2010; 11(4):1089-93B

Abstract

Candida antarctica lipase B (CALB) was found to be an efficient catalyst for copolymerization of diesters with amino-substituted diols to form poly(amine-co-esters) in one step. The copolymerization reactions were carried out at 50-100 degrees C in two stages: first stage oligomerization under 1 atm pressure of nitrogen followed by second stage polymerization under 1-2 mmHg vacuum. The formed copolymers possessed molecular weight (M(w)) up to 59000 and typical polydispersity (M(w)/M(n)) between 1.5 and 2.3. The enzymatic reaction appears to be quite general and accommodates a large number of comonomer substrates with various chain length and substituents. Thus, C(4)-C(12) diesters (i.e., from succinate to dodecanedioate) and diethanolamine comonomers with either an alkyl (methyl, ethyl, n-butyl, t-butyl) or an aryl (phenyl) substituent on nitrogen were successfully incorporated into the poly(amine-co-ester) chains. Biodegradable polyesters bearing tertiary amino groups have been reported to be efficient carriers for gene delivery. The high tolerance of the lipase toward tertiary amino functional groups as described in this paper provides new routes for synthesizing poly(amine-co-esters) with tailored structures for specific biomedical applications.

Authors+Show Affiliations

Biomedical Engineering Department, Yale University, 55 Prospect Street, New Haven, Connecticut 06511, USA. zhaozhong.jiang@yale.edu

Pub Type(s)

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

Language

eng

PubMed ID

20205448

Citation

Jiang, Zhaozhong. "Lipase-catalyzed Synthesis of Poly(amine-co-esters) Via Copolymerization of Diester With Amino-substituted Diol." Biomacromolecules, vol. 11, no. 4, 2010, pp. 1089-93.
Jiang Z. Lipase-catalyzed synthesis of poly(amine-co-esters) via copolymerization of diester with amino-substituted diol. Biomacromolecules. 2010;11(4):1089-93.
Jiang, Z. (2010). Lipase-catalyzed synthesis of poly(amine-co-esters) via copolymerization of diester with amino-substituted diol. Biomacromolecules, 11(4), pp. 1089-93. doi:10.1021/bm1000586.
Jiang Z. Lipase-catalyzed Synthesis of Poly(amine-co-esters) Via Copolymerization of Diester With Amino-substituted Diol. Biomacromolecules. 2010 Apr 12;11(4):1089-93. PubMed PMID: 20205448.
* Article titles in AMA citation format should be in sentence-case
TY - JOUR T1 - Lipase-catalyzed synthesis of poly(amine-co-esters) via copolymerization of diester with amino-substituted diol. A1 - Jiang,Zhaozhong, PY - 2010/3/9/entrez PY - 2010/3/9/pubmed PY - 2010/8/6/medline SP - 1089 EP - 93 JF - Biomacromolecules JO - Biomacromolecules VL - 11 IS - 4 N2 - Candida antarctica lipase B (CALB) was found to be an efficient catalyst for copolymerization of diesters with amino-substituted diols to form poly(amine-co-esters) in one step. The copolymerization reactions were carried out at 50-100 degrees C in two stages: first stage oligomerization under 1 atm pressure of nitrogen followed by second stage polymerization under 1-2 mmHg vacuum. The formed copolymers possessed molecular weight (M(w)) up to 59000 and typical polydispersity (M(w)/M(n)) between 1.5 and 2.3. The enzymatic reaction appears to be quite general and accommodates a large number of comonomer substrates with various chain length and substituents. Thus, C(4)-C(12) diesters (i.e., from succinate to dodecanedioate) and diethanolamine comonomers with either an alkyl (methyl, ethyl, n-butyl, t-butyl) or an aryl (phenyl) substituent on nitrogen were successfully incorporated into the poly(amine-co-ester) chains. Biodegradable polyesters bearing tertiary amino groups have been reported to be efficient carriers for gene delivery. The high tolerance of the lipase toward tertiary amino functional groups as described in this paper provides new routes for synthesizing poly(amine-co-esters) with tailored structures for specific biomedical applications. SN - 1526-4602 UR - https://www.unboundmedicine.com/medline/citation/20205448/Lipase_catalyzed_synthesis_of_poly_amine_co_esters__via_copolymerization_of_diester_with_amino_substituted_diol_ L2 - https://dx.doi.org/10.1021/bm1000586 DB - PRIME DP - Unbound Medicine ER -