Citation: Ning Zhu, Zi-Long Zhang, Wei He, Xiao-Cheng Geng, Zheng Fang, Xin Li, Zhen-Jiang Li, Kai Guo. Highly chemoselective lipase from Candida sp. 99-125 catalyzed ring-opening polymerization for direct synthesis of thiol-terminated poly(ε-caprolactone)[J]. Chinese Chemical Letters, ;2015, 26(3): 361-364. doi: 10.1016/j.cclet.2014.11.016 shu

Highly chemoselective lipase from Candida sp. 99-125 catalyzed ring-opening polymerization for direct synthesis of thiol-terminated poly(ε-caprolactone)

Ning Zhu ^a ,
Zi-Long Zhang ^a ,
Wei He ^a ,
Xiao-Cheng Geng ^a ,
Zheng Fang ^b ,
Xin Li ^a ,
Zhen-Jiang Li ^a,c ,
Kai Guo ^a,c,,

1.
a College of Biotechnology and Pharmaceutical Engineering, Nanjing Tech University, Nanjing 211816, China;
2.
b School of Pharmaceutical Sciences, Nanjing Tech University, Nanjing 211816, China;
3.
c State Key Laboratory of Materials-Oriented Chemical Engineering, Nanjing Tech University, Nanjing 211816, China

Corresponding author: Kai Guo,
Received Date: 29 August 2014
Available Online: 16 October 2014
Fund Project: the Priority Academic Program Development of Jiangsu Higher Education Institutions and China Postdoctoral Science Foundation (No. 2014M551574). (No. 2014AA021201)

Lipase from Candida sp. 99-125 catalyzed ring-opening polymerization of ε-caprolactone in the presence of 6-mercapto-1-hexanol was presented as a new metal-free approach for direct synthesis of welldefined thiol-terminated poly(ε-caprolactone). Remarkably, high chemoselectivity of lipase from Candida sp. 99-125 toward hydroxyl and thiol was exhibited and quantitative thiol fidelity over 90% was achieved. The tedious protecting/deprotecting steps for thiol and metal residue were avoided. The polymerizations with around 70% monomer conversion were conducted in bulk and toluene at relative low temperature of 40 ℃. Number-average molecular weight of resulted polymers ranged from 3000 to 4700 Da by changing the feed ratio between monomer and initiator. The structures of obtained thiolterminated poly(ε-caprolactone) were demonstrated by combining NMR and SEC analyses.
- Thiol,
- Poly(ε-caprolactone),
- Lipase from candida sp. 99-125,
- Chemoselective,
- Ring-opening polymerization
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