335080-98-3

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General Description

(carboxyl-⁽¹³⁾C)-anthranilic acid is a compound with a carboxyl group and a 13C isotope incorporated into the molecule. This chemical has potential applications in isotope labeling studies and nuclear magnetic resonance (NMR) spectroscopy. Anthranilic acid is a precursor for the synthesis of a variety of compounds, including dyes, pharmaceuticals, and agrochemicals. The addition of the carboxyl group and the 13C isotope to the anthranilic acid molecule can provide unique characteristics and properties for specific research and industrial purposes, particularly in the fields of organic chemistry and biochemistry.

Upstream product

• 1111-72-4 carbon dioxide 
• 615-36-1 2-bromoaniline 

Relevant academic research and scientific papers

Quinone methide chemistry of prekinamycins: 13C- labeling, spectral global fitting and in vitro studies

In this article, we address the presence of the prekinamycin quinone methide using the techniques of spectral global fitting and the 13C-labeling of the reactive centre. Two-electron reduction of a prekinamycin affords a long-lived quinone meth

Biosynthesis of aurachins A-L in Stigmatella aurantiaca: A feeding study

The isolation of aurachins A-L (1-11) from Stigmatella aurantiaca strain Sg a15 is described. Their structures and relative configurations were deduced from spectroscopic data, in particular NMR. Three structural types were identified: A-type aurachins (1, 2, 6) are C-3 oxygen-substituted quinolines carrying a farnesyl residue on C-4, C-type aurachins (3, 4, 7-11) are C-4 oxygen-substituted quinolines carrying a farnesyl residue on C-3, and C-type aurachin E (5) has a [1,1a,8,d]imidazoloquinoline structure. Feeding of 13C-labeled precursors showed that the quinoline ring is constructed from anthranihc acid and acetate, and the farnesyl residue from acetate by both the mevalonate and nonmevalonate pathways. Further, feeding of labeled aurachin C (3) indicated the A-type aurachins are derived by a novel intramolecular 3,4-migration of the farnesyl residue that is induced by a 2,3-epoxidation and terminated by a reduction step. 18O-Labeling experiments indicated the new oxygen substituents originate from atomospheric oxygen. On the basis of these results a biosynthetic scheme covering all aurachins is proposed. It is further proposed that quinolones with an unorthodox substitution pattern, such as the 2-geranylquinolones from Pseudonocardia sp. and the 3-heptylquinolones from Pseudomonas sp., are formed by related rearrangement mechanisms.