Use of singly and doubly labelled 13C-acetate in the elucidation of the structures and biosynthesis of multicolic and multicolosic acids, new tetronic acids from Penicillium multicolor

Use of singly and doubly labelled 13C-acetate in the elucidation of the structures and biosynthesis of multicolic and multicolosic acids, new tetronic acids from Penicillium multicolor
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DOI:
10.1039/c39740000636
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发表时间:
1974
期刊:
Journal of The Chemical Society, Chemical Communications
影响因子:
--
通讯作者:
Julian A. Gudgeon;J. S. Holker;T. J. Simpson
Julian A. Gudgeon;J. S. Holker;T. J. Simpson
中科院分区:
其他
文献类型:
--
作者:
Julian A. Gudgeon;J. S. Holker;T. J. Simpson

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从青霉菌培养物中分离的Multicolic和Multicolosic酸,通过1H-和13 C-n.m.r.显示分别具有结构(I)和(II),和紫外光谱研究,在O-甲基多醇酸甲酯(III)的光谱中观察到13 C-偶联,其由富含[1,2 - 13 C]乙酸酯的多醇酸制备,建立了特窗酸发色团中的取代模式;通过预先形成的芳族前体的氧化裂变,6-戊基间苯二甲酸,建议由13 C-n.m.r.富含[1- 13 C]-、[2- 13 C]-和[1,2 - 13 C]-乙酸酯的衍生物的光谱。
Multicolic and multicolosic acid, isolated from cultures of Penicillium multicolor, are shown to have structures (I) and (II) respectively by 1H- and 13C-n.m.r., and u.v. spectroscopic studies, 13C-couplings observed in the spectrum of methyl O-methylmulticolate (III), prepared from multicolic acid enriched with [1,2-13C]acetate establishing the substitution pattern in the tetronic acid chromophore; the biosynthesis of these metabolites from acetate, via oxidative fission of a preformed aromatic precursor, e.g., 6-pentylresorcylic acid, is suggested by the 13C-n.m.r. spectra of derivatives, enriched with [1-13C]-, [2-13C]-, and [1,2-13C]-acetate.