Journal ArticleDOI
Indolyl carboxylic acids by condensation of indoles with alpha-keto acids.
TLDR
The indole derivatives 2,2-bis(3,3'-indolyl)propionic acid (1); 1,1,1,-tris(3-3-,3"-indolyls)ethane (2); and 2-2-isocaproic acid (3) were isolated from solvent extracts of indole-supplemented supernatants of Escherichia coli and corynebacteria.Abstract:
The novel indole derivatives 2,2-bis(3,3'-indolyl)propionic acid (1); 1,1,1,-tris(3,3',3"-indolyl)ethane (2); and 2,2-bis(3, 3'-indolyl)isocaproic acid (3) were isolated from solvent extracts of indole-supplemented supernatants of Escherichia coli and corynebacteria. The compounds were also obtained by chemical synthesis: compounds 1 and 2 from indole and pyruvic acid and compound 3 from indole and alpha-ketoisocaproic acid, following incubation at 37 degrees C in aqueous medium. Tryptophan and pyruvic acid gave the novel 2-(2-tryptophanyl)lactic acid (4). The condensation reaction between indoles and alpha-keto acids was of general nature, and the mild reaction conditions suggested it may proceed in vivo. Examples for endogenous occurrence may be the neuro-degenerative diseases phenylketonuria and maple syrup urine disease, both characterized by elevated blood levels of alpha-keto acids.read more
Citations
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Journal ArticleDOI
Catalytic Functionalization of Indoles in a New Dimension
Marco Bandini,Astrid Eichholzer +1 more
TL;DR: This Review emphasizes the achievements in the selective catalytic functionalization of indoles (C-C bond-forming processes) over the last four years.
Journal ArticleDOI
Simple indole alkaloids and those with a nonrearranged monoterpenoid unit
Tomomi Kawasaki,Kazuhiro Higuchi +1 more
TL;DR: This review covers the literature on simple indole alkaloid and those with a nonrearranged monoterpenoid unit and newly isolated alkaloids, structure determinations, total syntheses and biological activities.
Journal ArticleDOI
Katalytische Funktionalisierung von Indolen in einer neuen Dimension
Marco Bandini,Astrid Eichholzer +1 more
TL;DR: In this paper, the Fortschritte hinsichtlich der selektiven katalytischen Funktionalisierung von Indolen (durch C-C-Kupplung) aus den vergangenen vier Jahre zusammen.
Journal ArticleDOI
Asymmetric Brønsted Acid Catalysis: Enantioselective Nucleophilic Substitutions and 1,4-Additions
Journal ArticleDOI
Molecular iodine-catalyzed efficient and highly rapid synthesis of bis(indolyl)methanes under mild conditions
TL;DR: Highly rapid and efficient electrophilic substitution reactions of indoles with various aldehydes and ketones were carried out using I2 in CH3CN to afford the corresponding bis(indolyl)methanes in excellent yields.
References
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Journal ArticleDOI
Indole-inducible proteins in bacteria suggest membrane and oxidant toxicity.
TL;DR: It is proposed that indole dissolved in membrane lipids, which caused membrane derangement and enabled direct interaction of redox-cycling isoprenoid quinones and dioxygen, resulting in the generation of superoxide.
Journal ArticleDOI
Maple syrup urine disease: it has come a long way.
TL;DR: Pulse-chase labeling in this system showed that a subset of E1 alpha mutations, notably the homozygous Y393N-alpha in Mennonite MSUD patients, impedes the assembly of the mutant E1alpha subunit with normal E1 beta in MSUD cells.