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Radical formation and coupling of hydroxycinnamic acids containing 1,2-dihydroxy substituents.

Abstract：

:Hydroxycinnamic acids involved in the deposition and cross-linking of plant cell-wall polymers do not usually contain 1,2-dihydroxy substituents, despite the presence of both 3,4-dihydroxycinnamic acid and 4,5-dihydroxy-3-methoxycinnamic acid as intermediates in the biogenesis of lignin. Since the O-methyl transferases, enzymes catalysing methylation, are targets for the genetic manipulation of lignin biosynthesis, the potential incorporation of these 1,2-dihydroxated substrates becomes increasingly significant. Using EPR spectroscopy, it was observed that 1,2-dihydroxy substituents did not have an inhibitory effect on radical formation. Increasing the extent of hydroxylation and methoxylation, resulted in an increased ease of substrate oxidation. Despite formation of the parent radicals, coupling did not proceed, under conditions that generally result in phenylpropanoid polymerisation. It is postulated that intermolecular radical-coupling reactions are inhibited due to rapid conversion to the o-quinone. In contrast, when methoxylated at C3, as in 4,5-dihydroxy-3-methoxycinnamic acid, radical coupling proceeds with the major product resulting from 8-O-3 radical coupling and formation of a substituted 2,3-dihydro-1,4-dioxin ring.

journal_name

Bioorg Chem

journal_title

Bioorganic chemistry

authors

Russell WR,Burkitt MJ,Scobbie L,Chesson A

doi

10.1016/s0045-2068(03)00042-7

subject

Has Abstract

pub_date

2003-06-01 00:00:00

pages

206-15

issue

3

eissn

0045-2068

issn

1090-2120

pii

S0045206803000427

journal_volume

31

pub_type

杂志文章

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