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Biosynthesis of Structurally Unique Fungal Metabolite GKK1032A2: Indication of Novel Carbocyclic Formation Mechanism in Polyketide Biosynthesis
journal contribution
posted on 2003-03-28, 00:00 authored by Hideaki OikawaThe biosynthesis of the antitumor agent GKK1032A2 (1) has been investigated by administration
of isotopically labeled (13C and 2H) precursors to Penicillium sp. GKK1032. These studies showed
that the backbone of 1 is constructed from l-tyrosine and a nonaketide chain flanked with five
methyl groups probably by a polyketide synthase and a nonribosomal peptide synthetase hybrid.
On the basis of the oxidation level of the starter unit and unusual 13-membered macroether
formation between the tyrosine hydroxy group and the polyketide chain, novel cyclization
mechanisms on the formation of a tricarbocyclic system and a macroether have been proposed.
Involvement of a similar type of cyclization in the biosynthesis of structurally related metabolites
is discussed.
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polyketide chainnonribosomal peptide synthetaseNovel Carbocyclic Formation Mechanismoxidation levelGKK 1032.antitumor agent GKK 1032A 2biosynthesimacroethernonaketide chainnovel cyclization mechanismsstarter unit13 Ctyrosine hydroxy groupPenicillium spmethyl groupspolyketide synthasePolyketide Biosynthesis2 Htricarbocyclic systemformation
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