Abstract：
: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.
journal_name
Bioresour Technoljournal_title
Bioresource technologyauthors
Gao WL,Liu H,Li N,Zong MHdoi
10.1016/j.biortech.2012.04.104subject
Has Abstractpub_date
2012-08-01 00:00:00pages
82-8eissn
0960-8524issn
1873-2976pii
S0960-8524(12)00750-Xjournal_volume
118pub_type
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