Regioselective enzymatic undecylenoylation of 8-chloroadenosine and its analogs with biomass-based 2-methyltetrahydrofuran as solvent.
2-Methyltetrahydrofuran (MeTHF), a biomass-derived compound, is a promising medium for biocatalysis and organometallic reactions. The regioselective acylation of 8-chloroadenosine (8-Cl-Ado) and its analogs was carried out in MeTHF with immobilized Penicillium expansum lipase. The lipase displayed more than twofold higher catalytic activity and much better thermostability in MeTHF than in other organic solvents and co-solvent systems. The optimum reaction medium, enzyme dosage, molar ratio of viny ester to nucleoside and reaction temperature for the enzymatic acylation of 8-Cl-Ado were MeTHF, 25 U/mL, 7.5 and 35 °C, respectively, under which the desirable 5'-O-undecylenoyl-8-Cl-Ado was obtained with a yield of 95% and a regioselectivity of >99% in 3 h. In addition, the lipase catalyzed regioselective undecylenoylation of other purine nucleosides, producing 5'-undecylenic acid esters with moderate to high yields (63-94%) and excellent 5'-regioselectivities (94->99%). Use of biomass-derived solvents might open up novel opportunities for sustainable and greener biocatalytic processes.
State Key Laboratory of Pulp and Paper Engineering, College of Light Industry and Food Sciences, South China University of Technology, Guangzhou 510640, China.
Wen-Li
WL
Gao
Huan
H
Liu
Ning
N
Li
Min-Hua
MH
Zong
D015762:2-Chloroadenosine / Q000031:analogs & derivatives* / Q000378:metabolism; D018533:Biomass; D004795:Enzyme Stability; D004800:Enzymes, Immobilized; D005663:Furans / Q000378:metabolism*; D008049:Lipase / Q000378:metabolism*; D009705:Nucleosides / Q000737:chemistry / Q000378:metabolism; D010407:Penicillium / Q000201:enzymology; D012997:Solvents / Q000378:metabolism*; D013237:Stereoisomerism; D013379:Substrate Specificity; D013696:Temperature
D004800:Enzymes, Immobilized; D005663:Furans; D009705:Nucleosides; D012997:Solvents; D015762:2-Chloroadenosine; D008049:Lipase; C550584:2-methyltetrahydrofuran; C075440:8-chloroadenosine