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(Received for publication, May 21, 1996)
From the Institute of Biological Chemistry, and Department of
Biochemistry and Biophysics, Washington State University,
Pullman, Washington 99164-6340
(
Volume 271, Number 38,
Issue of September 20, 1996
pp. 23262-23268
©1996 by The American Society for Biochemistry and Molecular Biology, Inc.
cDNA ISOLATION, CHARACTERIZATION, AND BACTERIAL EXPRESSION
OF A BIFUNCTIONAL DITERPENE CYCLASE INVOLVED IN RESIN ACID
BIOSYNTHESIS
)-Abietic acid, the principal
diterpenoid resin acid of the wound-induced oleoresin secreted by grand
fir (Abies grandis), is synthesized by the cyclization of
geranylgeranyl diphosphate to ()-abieta-7(8),13(14)-diene, followed
by sequential three-step oxidation of the C-18 methyl group of the
olefin to a carboxyl function. The enzyme catalyzing the cyclization
reaction, abietadiene synthase, was purified from stems of wounded
grand fir saplings and was digested with trypsin. Amino acid sequence
information from the resulting peptides allowed construction of
degenerate oligonucleotide primers, which amplified a 551-base pair
fragment from a wound-induced stem cDNA library. This hybridization
probe was then utilized to screen the wound-induced stem cDNA
library, from which three cDNA clones were isolated that were
functionally expressed in Escherichia coli, thereby
confirming that a single protein catalyzes the complex, multistep
cyclization of geranylgeranyl diphosphate to abietadiene. cDNA
isolate Ac22.1, which yielded the highest expressed level of cyclase
activity, was 2861 base pairs in length and encoded an 868-amino acid
open reading frame that included a putative plastidial transit peptide.
Deduced amino acid sequence comparison to other terpene cyclases
revealed an amino-terminal region of the abietadiene synthase, which
resembles those of enzymes that employ substrate double bond
protonation to initiate the carbocationic reaction cascade, and a
carboxyl-terminal region of the synthase, which resembles those of
enzymes that employ ionization of the substrate allylic diphosphate
ester function to initiate the cyclization reaction. This apparent
fusion of segments of the two distinct terpenoid cyclase types is
consistent with the novel mechanism of the bifunctional abietadiene
synthase in catalyzing both protonation-initiated and
ionization-initiated cyclization steps.
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