Enzyme-catalyzed ring-opening polymerization of ε-caprolactone using alkyne functionalized initiators

被引：15

作者：

Castano, Marcela ^{[1
]}

Zheng, Jukuan ^{[1
]}

Puskas, Judit E. ^{[1
]}

Becker, Matthew L. ^{[1
]}

机构：

[1] Univ Akron, Dept Chem & Biomol Engn, Akron, OH 44325 USA

来源：

POLYMER CHEMISTRY | 2014年 / 5卷 / 06期

基金：

美国国家科学基金会;

关键词：

COPPER-FREE; POLYESTERS; CHEMISTRY; POLY(EPSILON-CAPROLACTONE); CYCLOADDITIONS; TRANSESTERIFICATION; POLYCARBONATES; TEMPERATURE; POLYMERS; LACTONES;

D O I：

10.1039/c3py01536j

中图分类号：

O63 [高分子化学（高聚物）];

学科分类号：

070305 [高分子化学与物理];

摘要：

Well-defined poly(caprolactone)s were generated using alkyne-based initiating systems catalyzed by Candida antarctica Lipase B (CALB). Propargyl alcohol and 4-dibenzocyclooctynol (DIBO) were shown to efficiently initiate the polymerizations under metal free conditions and yielded 4 to 24 KDa polymers with relatively narrow molecular mass distribution. The alkyne bonds in the strained and unstrained initiating systems survived the polymerization conditions and the purification process. The resulting bonds can be sequentially functionalized post-polymerization using metal free and copper catalyzed click chemistry conditions.

引用

页码：1891 / 1896

页数：6

共 44 条

[1]

Recent developments in ring opening polymerization of lactones for biomedical applications [J].

Albertsson, AC ;

Varma, IK .

BIOMACROMOLECULES, 2003, 4 (06) :1466-1486

[2]

Mass-selective lipase-catalyzed poly(ε-caprolactone) transesterification reactions [J].

Bankova, M ;

Kumar, A ;

Impallomeni, G ;

Ballistreri, A ;

Gross, RA .

MACROMOLECULES, 2002, 35 (18) :6858-6866

[3]

Enzyme-Catalyzed Polymerization of End-Functionalized Polymers in a Microreactor [J].

Bhangale, Atul S. ;

Beers, Kathryn L. ;

Gross, Richard A. .

MACROMOLECULES, 2012, 45 (17) :7000-7008

[4]

Bornscheuer UT, 2006, HYDROLASES IN ORGANIC SYNTHESIS: REGIO- AND STEREOSELECTIVE BIOTRANSFORMATIONS, 2ND EDITION, P1

[5]

Directed differentiation and neurite extension of mouse embryonic stem cell on aligned poly(lactide) nanofibers functionalized with YIGSR peptide [J].

Callahan, Laura A. Smith ;

Xie, Sibai ;

Barker, Ian A. ;

Zheng, Jukuan ;

Reneker, Darrell H. ;

Dove, Andrew P. ;

Becker, Matthew L. .

BIOMATERIALS, 2013, 34 (36) :9089-9095

[6]

Green Polymer Chemistry VIII: Synthesis of Halo-ester-Functionalized Poly(ethylene glycol)s via Enzymatic Catalysis [J].

Castano, Marcela ;

Seo, Kwang Su ;

Kim, Eun Hye ;

Becker, Matthew L. ;

Puskas, Judit E. .

MACROMOLECULAR RAPID COMMUNICATIONS, 2013, 34 (17) :1375-1380

[7]

A Virtual Issue of Macromolecules: "Polymers from Renewable Resources" [J].

Coates, Geoffrey W. ;

Hillmyer, Marc A. .

MACROMOLECULES, 2009, 42 (21) :7987-7989

[8]

Lipase-catalyzed formation of end-functionalized poly(ε-caprolactone) by initiation and termination reactions [J].

Córdova, A ;

Iversen, T ;

Hult, K .

POLYMER, 1999, 40 (24) :6709-6721

[9]

Biocatalysis and enzymes in organic synthesis [J].

Davis, BG ;

Borer, V .

NATURAL PRODUCT REPORTS, 2001, 18 (06) :618-640

[10]

Insights into the initiation process of enzymatic ring-opening polymerization from monofunctional alcohols using liquid chromatography under critical conditions [J].

de Geus, Matthijs ;

Peters, Ron ;

Koning, Cor E. ;

Heise, Andreas .

BIOMACROMOLECULES, 2008, 9 (02) :752-757

← 1 2 3 4 5 →