Enzymatic synthesis solubility

Also the impact of various reaction parameters on enzymatic synthesis of amide surfactants from ethanolamine and diethanolamine has been studied, although the possibilities of acyl migration are not investigated. However, it was found that the selectivity of the reaction depended on the solubility of the product in the solvent used, and that the choice of solvent was critical to obtain an efficient process [17]. 

C. Oligo- and Poly-nucleotides.—The stepwise enzymatic synthesis of internucleotide bonds has been reviewed. A number of polynucleotides containing modified bases have been synthesised " in the past year from nucleoside triphosphates with the aid of a polymerase enzyme, and the enzymatic synthesis of oligodeoxyribonucleotides using terminal deoxynucleotidyl transferase has been studied. Primer-independent polynucleotide phosphorylase from Micrococcus luteus has been attached to cellulose after the latter has been activated with cyanogen bromide. The preparation of insolubilized enzyme has enabled large quantities of synthetic polynucleotides to be made. The soluble enzyme has been used to prepare various modified polycytidylic acids. ... 

Among the aldonolactone-based surfactants are aldonolactone-linked fatty esters which have been prepared by selective acylation of unprotected aldono-1,4-lac-tones or aldono-1,5-lactones, One of the first reported examples of this type of surfactant was applied to the enzymatic synthesis of 6-0-aUcanoylgluconolactones [35], Thus, 6-0-decanoyl- and 6-0-dodecanoyl- derivatives (21a and 21b, respectively, Scheme 8) were obtained in 26-27% yield by esterification of glucono-1,5-lactone (1) at C-6 with the corresponding 2,2,2-trichloroethyl carboxylate in the presence of porcine pancreatic lipase (PPL) as catalyst. Compounds 21a,b are soluble in water at 90-96°C but precipitate when cooled to 30-37°C, NMR and GC-MS analysis after dissolution and precipitation indicated the presence in the mixture of compound 21b, the glucono-1,4-lactone-derived ester 22, and the... 

Oxireductases in the Enzymatic Synthesis of Water-Soluble Conducting Polymers... 

Alva KS, Kumar J, Marx KA, Tripathy SK (1997) Enzymatic synthesis and characterization of a novel water-soluble polyanihne poly(2,5-diaminobenzenesulfonate). Macromolecules 30(14) 4024 029... 

Rumbau V, Pomposo JA, Eleta A, Rodriguez J, Grande H, Mecerreyes D, Ochoteco E (2007) Eirst enzymatic synthesis of water-soluble conducting poly(3,4-ethylenedioxythiophene). Biomacromolecules 8(2) 315-317... 

Luthi, P. and Luisi, P. L. (1984). Enzymatic-synthesis of hydrocarbon-soluble peptides with reverse micelles. / Am. Chem. Soc., 106, 7285-6. 

In 2002, Do et al. [85] proposed a pathway for the enzymatic synthesis of (-)-menthyl a-maltoside and a-maltooligosides from (-)-menthyl a-glucoside using cyclodextrin glucanotransferase obtained from Bacillus macerans. The reaction can be performed in a reactor containing (-)-menthyl a-glucoside, the enzyme and soluble starch the yield was about 80% 15% (-)-menthyl a-malto-side and 65% (-)-menthyl a-maltooligosides, respectively. Treatment of the starch with a-amylase can raise the proportion of (-)-menthyl a-maltoside. 

More recently, the chemo-enzymatic synthesis of inulin-containing hydrogels was reported [54]. The key point was the solubility of inulin [a mixture of oligomers and polymers containing 2-60 (or more) 5-2,1 linked D-fructose molecules having a glucose unit as the initial residue] in dimethylformamide (DMF), a fact that allowed its esterification by action of a protease from Bacillus subtilis. 

For charged products the situation is significantly different. For many reactions involving zwitterions, the presence of undissolved substrates did not lead to precipitated products in enzymatic synthesis reactions [11]. These observations are related to differences in the solubility properties of zwitterions as compared to acids, bases, or uncharged compounds. Because of the low concentration of the... 

Nabid MR, Entezami AA (2003) Enzymatic synthesis and characterization of a water-soluble, conducting poly(o-toluidine). Eur Polym J 39 1169-1175... 

Oguchi, T., Tawaki, S., Uyama H., and Kobayashi, S. 2000. Enzymatic synthesis of soluble polyphenol. Bull. Chem. Soc. Jpn., 73,1389-1396. 

Potato phosphorylase has successfully been employed for the enzymatic synthesis of 2-deoxyglucosyl 1-phosphate 135 (Scheme 45) [252]. D-glucal 136 was transferred onto maltotetrose 137 in the presence of the phosphorylase and catalytic amounts of phosphate to afford a modified maltooligosaccharide 138 that contained 2-deoxy-D-arabino-hexopyranosyl residues [253]. Formation of 2-deoxyglucosyl phosphate 135 can be explained by reverse phosphorolysis of the oligosaccharide 138. When soluble starch was employed as primer and an equimolar amount of phosphate was added, 2-deoxyglucosyl phosphate 135 was obtained in 50% isolated yield on a preparative scale. 

Enzymatic synthesis of cellulose has been achieved by cel-lulase. For example, incubation of fS-cellobiosyl fluoride with a cellulase from Trichoderma viride can produce cellulose in 54% yield with DP around 22 after 12h. In addition, change of the reaction conditions (substrate concentration or organic solvent concentration) enabled the selective synthesis of the water-soluble celloohgosaccharides (118). 

Solution phase supports have the problem of product recovery. An alternative approach is to couple the substrate to a water-soluble polymer that can be removed from solution by precipitation of the polymer or size exclusion chromatography. Water-soluble supports have been used in the enzymatic synthesis of pseudo-GM3 (118). 

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