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J Biol Chem, Vol. 274, Issue 50, 35483-35491, December 10, 1999
§¶
,

From the The final step in the biosynthesis of the
cyanogenic glucoside dhurrin in Sorghum bicolor is the
transformation of the labile cyanohydrin into a stable storage form by
O-glucosylation of
(S)-p-hydroxymandelonitrile at the cyanohydrin
function. The
UDP-glucose:p-hydroxymandelonitrile-O-glucosyltransferase was isolated from etiolated seedlings of S. bicolor
employing Reactive Yellow 3 chromatography with UDP-glucose elution as
the critical step. Amino acid sequencing allowed the cloning of a full-length cDNA encoding the glucosyltransferase. Among the few characterized glucosyltransferases, the deduced translation product showed highest overall identity to Zea mays
flavonoid-glucosyltransferase (Bz-Mc-2 allele). The
substrate specificity of the enzyme was established using isolated
recombinant protein. Compared with endogenous
p-hydroxymandelonitrile, mandelonitrile, benzyl alcohol, and benzoic acid were utilized at maximum rates of 78, 13, and 4%,
respectively. Surprisingly, the monoterpenoid geraniol was glucosylated at a maximum rate of 11% compared with
p-hydroxymandelonitrile. The picture that is emerging
regarding plant glucosyltransferase substrate specificity is one of
limited but extended plasticity toward metabolites of related
structure. This in turn ensures that a relatively high, but finite,
number of glucosyltransferases can give rise to the large number of
glucosides found in plants.
Department of Horticulture, Viticulture, and
Oenology, the University of Adelaide, Waite Campus PMB1,
Glen Osmond SA 5064, South Australia, Australia, the
§ Plant Biochemistry Laboratory, Department of Plant
Biology, The Royal Veterinary and Agricultural University, the
¶ Center for Molecular Plant Physiology (Place), The Royal
Veterinary and Agricultural University, 40 Thorvaldensvej,
DK-1871 Frederiksberg C, Copenhagen, Denmark, and the

Australian Wine Research Institute,
P. O. Box 197, Glen Osmond SA 5064, South Australia, Australia
The nucleotide sequence(s) reported in this paper has been submitted to the GenBankTM/EMBL Data Bank with accession number(s) AF199453.
Recipient of an Australian Postgraduate award.
**
To whom correspondence should be addressed. Tel.: 45-35283352; Fax:
45-35283333; E-mail: blm@kvl.dk.
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