The E/Z isomerization step in the biosynthesis of Z coniferyl alcohol in Fagus grandifolia Ehrh.

In nature, it has long been assumed that p-hydroxycinnamyl alcohols occur exclusively in their trans (E) stereoisomeric form. However, in beech bark (Fagus grandifolia Ehrh.) only the corresponding cis (Z) monomers were found. Experiments with beech bark and 2-¹⁴C-labelled E ferulic acid, E coniferaldehyde, and E coniferyl alcohol revealed that these compounds were efficiently incorporated into both E and Z isomers of coniferyl alcohol. On the other hand, low incorporation of 2-¹⁴C-labelled Z ferulic acid indicated that this isomer was not a preferred substrate. Our results suggest that Z coniferyl alcohol is produced by E + Z isomerization of the corresponding E isomer. Experimental evidence excluded the possibility of this unusual isomerization occurring by either chemical or photochemical means; instead it is concluded that isomerization is enzymatically mediated by a novel isomerase.

Name thesis:degree_name

M.S.

Level thesis:degree_level

masters

Discipline thesis:degree_discipline

Forest Products

Department dc:contributor.department

Forest Products

Grantor dc:publisher

Virginia Polytechnic Institute and State University

Year dc:date.issued

1987

Author dc:creator

• Dubelsten, Paul

Statement dc:rights

• In Copyright

Licence dc:rights.uri

• http://rightsstatements.org/vocab/InC/1.0/

Language dc:language.iso

en

Handle dc:identifier.uri

http://hdl.handle.net/10919/101178

OAI identifier oai:identifier

oai:vtechworks.lib.vt.edu:10919/101178