Author
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Ludley, Frank |
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Ralph, John |
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Submitted to: American Chemical Society Abstracts
Publication Type: Abstract Only Publication Acceptance Date: 3/28/1996 Publication Date: N/A Citation: N/A Interpretive Summary: Technical Abstract: Grass lignins contain a significant amount of p-coumarate. We have recently shown that p-coumarate is esterified entirely by the gamma position of the lignin sidechain, implicating coniferyl and sinapyl p-coumarate as precursors in the lignification. In order to better understand this process, and determine why the p-coumarate moiety does not participate in the radical reactions (it remains free-phenolic), coniferyl and sinapyl p- coumarate were required for biomimetic lignification studies. Unfortunately, both compounds are not particularly stable and are water- insoluble. Consequently, the glucosides have been targeted; beta- glucosidases can release the phenols for radical incorporation. Such glucosides may also be the compounds shuttled to the cell wall in the natural process. Preparation of the glucosides of various alcohol and acid monomers is described along with modified coupling procedures to produce the ester. The most difficult step is deprotection to produce the final hydroxycinnamyl p-coumarate di-glucosides. |
