Acrylic acid Enzymatic hydrolysis

One difficulty associated with polymer-based gene therapy is that delivery efficiency is generally low, due to redirection of the polymer complexes to and enzymatic hydrolysis of the DNA in the lysosome, rather than release of DNA from the endosome (see Figure 2). A strategy to circumvent this is to include polymers that disrupt the endosomal membrane. This is achieved if they are active i.e. protonated) at pH 6.5 or below, but inactive (deprotonated) at pH 7.4, since the endosomal pH is around one unit lower than the cytoplasm. Hoffman, Tirrell and co-workers have developed synthetic polymers such as poly(alkyl acrylic acid)s and poly(acrylate-co-acrylic acid)s that show en-... 

The acidic form of classical sophorolipid (a deacetylated compound) produced by alkaline hydrolysis of the native lactonic form (Fig. 2) was successfully converted by enzymatic biotransformation (glycosidase catalysis) to an acidic glucose lipid [44]. Another modification was performed with alkyl-amines leading to alkylamides of the acidic sophorolipid [123]. Bisht et al. [128] reported an efficient chemoenzymatic route that led to an 6-O-acryloyl-sophorolipid macrolactone analog. The homopolymerization of this monomer as well as its copolymerization with acrylic acid and acrylamide led in maximum to a molecular weight of 4.2 x 10" Da. The first total synthesis of a major component of the microbial classical lactonic sophorolipid was described by Fiirstner et al. [129]. 

A similar dependence of the configuration of the product on the ( /Z)-configu-ration of the substrate was observed during the yeast-mediated reduction of 2-chloro-acrylate esters [1016]. Whereas the chiral recognition of the (Z)-alkenes was perfect, the (Ej-isomers gave products with lower e.e. In addition, it was shown that the microbial reduction took place on the carboxylic acid stage, which were formed enzymatically by hydrolysis of the starting esters prior to the reduction step [1017] (Scheme 2.138). 

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