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Asian Journal of Biological Sciences
Year: 2011  |  Volume: 4  |  Issue: 2  |  Page No.: 157 - 165

Absolute Configuration of Syringylglycerol-8-O-4’-(Sinapyl Alcohol) Ethers, Neolignans as Well as Lignin Substructure Dimeric Compounds in Higher Plants

S. Alam, T. Suzuki and T. Katayama    

Abstract: Syringylglycerol-8-O-4'-(sinapyl alcohol) ethers (SGSEs) are lignin substructure dimeric compounds or 8-O-4' neolignans. To investigate biosynthesis of the 8-O-4' neolignans, incubation of sinapyl alcohol (SA) with enzyme preparations of Eucommia ulmoides was performed and formation of optically active SGSEs was found. To clarify the stereochemical mechanism of the SGSE formation, absolute configuration of four stereoisomers, (+)-erythro, (–)-erythro, (+)-threo and (–)-threo isomers, of SGSEs that contain a chiral secondary benzyl alcohol were determined as (7R, 8S), (7S, 8R), (7S, 8S) and (7R, 8R), respectively, by Mosher’s method [1H NMR analysis of tri-(R)-(+)-α-methoxy-α-trifluoromethylphenylacetate (MTPA) of SGSEs] with our related empirical rules. Four stereoisomers of SGSEs were obtained by dehydrogenations of SA with FeCl3 followed by reversed phase HPLC and chiral HPLC.

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