Biosynthesis of isoxazolin-5-one and 3-nitropropanoic acid containing glucosides in juvenile Chrysomelina

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Biosynthesis of isoxazolin-5-one and 3-nitropropanoic acid containing glucosides in juvenile Chrysomelina.

Stable-isotope-labeled precursors were used to establish the biosynthetic pathway leading from β-alanine towards isoxazolin-5-one glucoside 1 and its 3-nitropropanoate (3-NPA) ester 2 in Chrysomelina larvae. Both structural elements originate from sequestered plant-derived β-alanine or from propanoyl-CoA that is derived from the degradation of some essential amino acids, e.g. valine. β-Alanine ...

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Synthesis and photosensitivity of isoxazolin-5-one glycosides.

A novel procedure for the synthesis of isoxazolin-5-one glycosides starting from unprotected carbohydrates is described. The substrate scope of the one-pot synthetic protocol was explored using D-configured glucose, xylose, maltose, fructose, ribose and 2-deoxyribose. Naturally occurring 2-(β-D-glucopyranosyl)-3-isoxazolin-5-one and four novel isoxazolin-5-one glycosides derived from xylose, ma...

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4-methylideneimidazole-5-one-containing aminomutases in enediyne biosynthesis.

Many natural products contain unusual aromatic β-amino acids or moieties derived therefrom. The biosynthesis of these β-amino acids was first elucidated during a biosynthetic study of the enediyne antitumor antibiotic C-1027, when an enzyme, SgcC4, was discovered to convert L-tyrosine to (S)-β-tyrosine. SgcC4 is similar in sequence and structure to 4-methylideneimidazole-5-one (MIO)-containing ...

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species. Similar findings have previously been reported for M. piperita (Bricout & Paupardin, 1975) and M. rotundifolia (Bricout et al., 1978). Many of the calluses accumulate only the early precursors of the monoterpenes (namely geraniol, linalol and lavandulol), but some species give rise to cultures that accumulate monoterpenes characteristic of the intact plant. For example, cell lines from...

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The biosynthesis of phenolic glucosides in plants.

Kamil, I. A., Smith, J. N. & Williams, R. T. (1953b). Biochem. J. 54, 390. McGuire, J. S. & Tomkins, G. M. (1960). J. biol. Chem. 235, 1634. Miura, S. (1911). Biochem. Z. 36, 25. Neubauer, 0. (1901). Arch. exp. Path. Pharmak. 46, 133. Ofner, P. (1955). Biochem. J. 61, 287. Roy, A. B. (1956). Biochem. J. 63, 294. Sie, H. & Fishman, W. H. (1957). J. biol. Chem. 225, 453. Taylor, W. (1954). Bioche...

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ژورنال

عنوان ژورنال: Organic & Biomolecular Chemistry

سال: 2016

ISSN: 1477-0520,1477-0539

DOI: 10.1039/c6ob00899b