4-Hydroxy-2-pyrone formation by chalcone and stilbene synthase with nonphysiological substrates.

Abstract:

:Valerophenone synthase (VPS) is a polyketide synthase that catalyzes the formation of the phloroglucinol derivatives in the synthesis of the bitter acids in hop (Humulus lupulus). The reaction uses isovaleryl-CoA or isobutyryl-CoA, but otherwise it is identical to that of the chalcone synthase in flavonoid biosynthesis. Our study showed that chalcone synthase can perform the function of VPS, but not perfectly, because the majority of the reactions terminated after two condensation reactions (products: 4-hydroxy-2-pyrone derivatives). The same experiments with stilbene synthase yielded exclusively the 4-hydroxy-2-pyrone derivatives, not the products expected from three condensation reactions. The results are discussed in the context of the functional diversity and evolution in the family of CHS-related polyketide synthases.

journal_name

Phytochemistry

journal_title

Phytochemistry

authors

Zuurbier KW,Leser J,Berger T,Hofte AJ,Schröder G,Verpoorte R,Schröder J

doi

10.1016/s0031-9422(98)00346-x

subject

Has Abstract

pub_date

1998-12-01 00:00:00

pages

1945-51

issue

7

eissn

0031-9422

issn

1873-3700

pii

S0031-9422(98)00346-X

journal_volume

49

pub_type

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