Biocatalytic Synthesis of Sugar-Containing Polyacrylates
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https://orcid.org/0000-0003-2219-5833
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Article
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ENG
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Abstract
Achemoenzymaticapproachhasbeendevelopedtopreparemonosaccharide-basedpoly-(acrylate)s.ThelipasefromPseudomonascepaciacatalyzedthetransesterificationofavarietyofmonosaccharideswithvinylacrylateinpyridinetogivethe6-acryloylesters.TheacrylateesterswerepolymerizedinDMFwithAIBNtogivethepoly(acrylate)products.Suchasyntheticstrategyhasledtothesynthesisofpoly(methyl6-acryloyl-j3-galactoside)withMw=135000andMa=58000forapolydispersityof2.3.Theoverallyieldfrommethyl0-galactosidewas56%.Thepolymerwashighlywatersolubleandsolubleinpolarorganicsolvents.Replacingthemethylaglyconwithphenylor2-nitrophenylmoietiesresultedinpolymerswithpoorwatersolubilitiesandimprovedorganicsolventsolubilities.Inthecaseofthephenylaglyconthepolymerwaspreparedin40%isolatedyieldfromphenyljS-galactoside.Thepoly(phenyl6-acryloyl-/3-galactoside)hadanAf,=52700andanMn=28900forapolydispersityof1.8.Additionofethyleneglycoldimethacrylateasacross-linkerduringAIBN-catalyzedpolymerizationinDMFresultedinwater-insolublepolymersthatswelledinaqueoussolution.Inthepresenceof0.3%cross-linker,apoly(methyl6-acryloyl-/3-galactoside-hema)copolymerswelledtocontain98%waterand,hence,holdnearly50-folditsweightinwater.Suchmaterialsmaybeusefulasbiocompatiblehydrogelsforbiomedicalandmembraneapplications
Description
Macromolecules, 25, 7081-7085
Note : if this item contains full text it may be a preprint, author manuscript, or a Gold OA copy that permits redistribution with a license such as CC BY. The final version is available through the publisher’s platform.
Note : if this item contains full text it may be a preprint, author manuscript, or a Gold OA copy that permits redistribution with a license such as CC BY. The final version is available through the publisher’s platform.
Full Citation
Biocatalytic Synthesis of Sugar-Containing Polyacrylates, B.D. Martin, S.A. Ampofo, R.J. Linhardt, J.S. Dordick, Macromolecules, 25, 7081-7085 (1992).