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Stereochemistry of erythro- and threo-syringylglycerol-8-O-4?-(sinapyl alcohol) ethers and their enzymatic formation with optical activity in Eucommia ulmoides


Md. Shameul Alam, Deeder Sultana, Toshisada Suzuki and Takeshi Katayama.

Cited by (1)

Abstract
In this study an enzymatic system, horseradish peroxidase (HRP)-hydrogen peroxide was used as catalysts for the enzymatic formation of enantiospecific syringulglycerol-8-O-4? (sinapyl alcohol) ethers (SGSEs) from enzyme preparations of Eucommia ulmoides with sinapyl alcohol (SA) as a monolignol precursor. Reversed phase HPLC analysis of the erythro- and threo-SGSE showed that the ratio of erythro: threo was 47: 53. Both isomers were isolated by HPLC and their structural confirmation was done by 1H NMR spectra. Chiral column HPLC analysis of the erythro- and threo-SGSE showed that their enantiomeric compositions were as follows: (+)-erythro: (-)-erythro = 46.7:53.3 (6.6% e.e), and (+)-threo: (-)-threo = 45.2: 54.8 (9.6% e.e). To elucidate the stereochemistry of erythro and threo- SGSEs, we have determined absolute configurations of the four stereoisomers, (+)-erythro-, (-)-erythro-, (+)-threo-, and (-)-threo-SGSEs as (7R, 8S), (7S, 8R), (7S, 8S), and (7R, 8R), respectively, by Mosher's method through the 1H NMR spectroscopy of (+)-(R)-?-methoxy- ?- trifluoromethylphenylacetate (MTPA) esters of ?, ? and ?' positions.

Key words: Stereochemistry, SGSE, erythro, threo, MTPA, soluble enzyme, Eucommia ulmoides



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