NASA Logo

NTRS

NTRS - NASA Technical Reports Server

Back to Results
On the Stereoselective Synthesis of (+)-Pinoresinol in Forsythia Suspensa from its Achiral Precursor, Coniferyl AlcoholThe residue from Forsythia suspensa stems, upon removal of soluble enzymes, has provided the first evidence for a stereoselective coupling enzyme in lignan biosynthesis. This preparation catalyses the preferred formation (ca 65%) of (+)-[8,8'- C-14] pinoresinol from [8-C-14]coniferyl alcohol in the absence of exogenously provided cofactors; addition of H2O2 had little effect on enantiomeric composition. However, when NAD and malate were supplied, the stereoselectivity of the coupling reaction was significantly enhanced and pinoresinol consisting of ca 80% of the (+)-antipode was obtained. Clearly, the insoluble residue contains a specific coupling enzyme which catalyses (+)-pinoresinol formation from coniferyl alcohol. By contrast, when [8- C-14] sinapyl alcohol was employed as substrate, only racemic syringaresinols were formed: this non-stereoselective peroxidase-catalysed coupling reaction presumably accounts for the low levels of (-)-pinoresinol encountered in this system when coniferyl alcohol is used as a substrate.
Document ID
19970023972
Acquisition Source
Kennedy Space Center
Document Type
Reprint (Version printed in journal)
Authors
Davin, Laurence B.
(Washington State Univ. Pullman, WA United States)
Bedgar, Diana L.
(Washington State Univ. Pullman, WA United States)
Katayama, Takeshi
(Washington State Univ. Pullman, WA United States)
Lewis, Norman G.
(Washington State Univ. Pullman, WA United States)
Date Acquired
August 17, 2013
Publication Date
January 1, 1992
Publication Information
Publication: Phytochemistry
Publisher: Pergamon Press Ltd.
Volume: 31
Issue: 11
ISSN: 0031-9422
Subject Category
Chemistry And Materials (General)
Report/Patent Number
NASA-CR-204931
NAS 1.26:204931
Accession Number
97N72225
Funding Number(s)
CONTRACT_GRANT: USDA-91-3710-3-6638
CONTRACT_GRANT: NAG10-0086
Distribution Limits
Public
Copyright
Public Use Permitted.
Document Inquiry

Available Downloads

There are no available downloads for this record.
No Preview Available