Lipase-catalyzed synthesis of poly

Hayes, D.G. Lipase-catalyzed synthesis of poly-hydric alcohol-poly(ricinoleic acid) ester star polymers. Polym. Prepr. (Am. Chem. Soc., Div. Polym. Chem.) 2005, 46 (1), 276-277. 

Lipase-catalyzed synthesis of poly(l,4-butyl sebacate) from reactions of 1,4-butanediol and sebacic acid or activated derivatives of sebacic acid were studied by Linko et al. [51]. Reactions between 1,4-butanediol with sebacic acid,... 

The phase separation of reactants hindered attempts to carry out lipase-catalyzed synthesis of poly(butylene succinate) (PBS) from succinic acid and 1,4-butanediol via dehydration. Therefore, in order to obtain a monophasic reaction mixture, dimethyl succinate was used in place of succinic acid. [49] The reaction mixture remained monophasic during the reaction course, and after 21 h at 95 °C PBS with M of 38000 was obtained. 

Scheme 4.27 Pseudomonas fluorescens lipase-catalyzed synthesis of poly (MBC-co-TMC).

J. (1995) Lipase-catalyzed synthesis of poly(1,4-butyl sebacate) from sebacic acid or its derivatives with 1,4-butanediol./. Biotechnol., 40 (2), 133-138. 

Scheme 11.1 Lipase-catalyzed synthesis of poly(L-lactide) (10).

General procedure for the lipase-catalyzed synthesis of poly(l,8-octanyladipate-co-sorbityladipate) terpolyesters ... 

Lipase-Catalyzed Synthesis of Poly(Hydroxy Acid) Esters... 

Azim, H., Dekhterman, A., Jiang, Z., and Gross, R.A. (2006) Candida antarctica lipase B-catalyzed synthesis of poly(butylene succinate) shorter chain building blocks also work. Biomacromolecules, 7 (11), 3093-3097. 

Jiang, Y., Liu, C., and Gross, R.A. (2008) Lipase-catalyzed synthesis of aliphatic poly(carbonate-co-esters). Macromolecules, 41 (13), 4671-4680. 

Candida antarctica Lipase B Catalyzed Synthesis of Poly(butylene succinate) Shorter Chain Building Blocks Also Work... 

The fatty esters of polyethers are known to be good surfactants, and many commercial products are available in the market place. Most people use chemical methods to achieve the required synthesis. Enzymatic methods can also be used however, the reaction needs to be optimized. An example is the lipase-catalyzed synthesis of fatty acid diester of poly(ethylene glycol) EG). 

Kelly, A.R., Hayes, D.G., 2006. Lipase-catalyzed synthesis of polyhydric alcohol-poly(ricinoleic add) esta- star polymars. J. Appl. Polym. Sci. 101, 1646-1656. 

Poly(malic acid) is a biodegradable and bioadsorbable water-soluble polyester having a carboxylic acid in the side chain. The chemoenzymatic synthesis of poly(malic acid) was achieved by the lipase-catalyzed polymerization of benzyl (3-malolactonate, followed by the debenzylation. The molecular weight of poly(benzyl (3-malolactonate) increased on copolymerizafion with a small amount of (3-PL using lipase CR catalyst. ... 

Chemoenzymatic synthesis of biodegradable poly(malic acid) was performed by lipase-catalyzed polymerization of benzyl /J-malolactone, followed by the debenzylation [72]. The addition of a small amount of /J-PL (17 mol % for the monomer) increased Mw up to 3 x 104 [73]. 

Feng Y, Klee D, Keul H, Hdcker H (2000) Lipase-catalyzed ring-opening polymerization of morpholine-2,5-dione derivatives a novel route to the synthesis of poly(ester amide)s. Macromol Chem Phys 201 2670-2675... 

Ester synthesis of fatty acid ethyl ester. The lipase-catalyzed esterification of fatty acid and alcohol is well-known. It was also favorable for the esterification of poly unsaturated fatty acids under mild conditions with the enzyme. However, the activity of native lipase is lower in polar organic solvents, i.e. ethanol and methanol. The synthesis of Ae fatty acid ethyl ester was carried out in ethanol using the palmitic acid-modified lipase. As shown in Figure 7, the reactivity of the modified lipase in this system was much higher than that of the unmoditied lipase. 

He, F., Wang, Y., Feng,)., Zhuo, R., and Wang, X. (2003) Synthesis of poly[(5 -benzyloxy-trimethylene carbonate) -co - (5,5 - di methyl-trimethylene carbonate)] catalyzed by immobilized lipase onsilica particles... 

Poojari, Y. Clarson, S. J., Lipase Catalyzed Synthesis and Thermal Properties of Poly(dimethylsiloxane)-Poly(ethylene glycol) Amphiphilic Block Copolymers. J. Inorg. Organomet. Polym. 2010,20, 46-52. 

Single-step synthesis of polyester macromonomers was achieved by lipase-catalyzed polymerization of lactones in the presence of vinyl esters acting as terminator ( terminator method ) (187,188). A methacryl-type poly(DDL) macromonomer was obtained using vinyl methacrylate (12.5 or 15 mol% based on DDL) and lipase PF as terminator and catalyst, respectively. By the addition of divinyl sebacate, the telechelic polyester having a carboxylic acid group at both ends was synthesized. 

Lipase CA catalyzed the polymerization of cyclic dicarbonates, cyclo-bis(hexamethylene carbonate) and cyclobis(diethylene glycol carbonate), to give the corresponding polycarbonates (214). The enzymatic copolymerization of cy-clobis(diethylene glycol carbonate) with DDL produced a random ester-carbonate copolymer. Enzymatic synthesis of poly(ester-carbonate) was also achieved by the copolymerization of l,3-dioxan-2-one and lactide (215). The PPL-catalyzed copolymerization at 100°C produced the copolymer with My, higher than 2x 10. ... 

Scheme 2.3 Lipase (Novozym-435)-catalyzed synthesis of silicone fluorinated aliphatic polyesteramides (SFAPEAs) by transesterification and amidation of a,0)-aminopropyl terminated poly(dimethylsiloxane) (APDMS) and 3,3,4,4,5,5,6,6-octafluoro 1,8-octanediol (OFOD) with diethyl adipate (DBA), respectively, at temperatures in the range of 70°C to 90°C in the bulk [23], Reproduced with permission (Copyright 2010, Elsevier).

Scheme 2.4 Lipase (Novozym-435)-catalyzed synthesis of silicone aromatic polyester (SAPE) by polyesterification of a,(W-(dihydroxy alkyl)-terminated poly(dimethylsiloxane) (m = 7, n = 30 and = 2500 g mol ) with dimethyl terephthalate in toluene at 80°C under reduced pressure [26]. Reproduced with permission (Copyright 2009, The Royal Society of Chemistry).

The enzymatic polymerization of 12-hydroxydodecanoic acid in the presence of 11-methacryloylaminoundecanoic acid conveniently produced the methacrylamide-type polyester macromonomer. Lipases CA and CC were active for the macromonomer synthesis. Enzymatic selective monosubstitution of a hydroxy-functional dendrimer was demonstrated. Lipase CA-catalyzed polymerization of 8-CL in the presence of the first generation dendrimer gave the poly(8-CL)-monosubstituted dendrimer. 

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