Synthesis of betalamic acid

Buechi, George; Fliri, Hans; Shapiro, Rafael

doi:10.1021/jo00432a048

Cited by 26 publications

(15 citation statements)

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“…To date, most of the protocols applied for purifying betalamic acid involve multiple steps and very low yields [38,39]. However, in this paper, purification of betalamic acid has been carried out by a straightforward batch method that allows pure betalamic acid to be obtained in preparative amounts.…”

Section: Fluorescent Staining Of Proteins With Red Beet Root Juicementioning

confidence: 99%

Fluorescent bioinspired protein labeling with betalamic acid. Derivatization and characterization of novel protein-betaxanthins

et al. 2016

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Section: Fluorescent Staining Of Proteins With Red Beet Root Juicementioning

confidence: 99%

Fluorescent bioinspired protein labeling with betalamic acid. Derivatization and characterization of novel protein-betaxanthins

et al. 2016

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“…Betalamic acid can be chemically synthesised (Büchi et al, 1977) in a procedure that involves multiple steps and gives low yields. Other authors obtained the acid from the degradation products of natural betanin (betanidin-5-O-β-glucoside; Wyler et al, 1965;Kimler et al, 1971), but the problem in this case is the presence of the other degradation product, cyclo-DOPAglucoside, which is able to reverse the reaction (Huang and von Elbe, 1985).…”

Section: Introductionmentioning

confidence: 99%

Development of a protocol for the semi‐synthesis and purification of betaxanthins

García-Carmona

Escribano

2006

Phytochemical Analysis

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A method for the analytical and semi-preparative chromatographic purification of betaxanthins is described together with an improved procedure for the semi-synthesis of these compounds from betalamic acid. Standard conditions for obtaining preparative amounts of betaxanthins free of the precursor amino acids are provided. Following this procedure, 14 pure betaxanthins were obtained with yields of up to 100%. A simple reversed-phase HPLC protocol for pigment identification and quantification is also provided. Calibration for betaxanthins is reported for the first time using the synthesised and purified pigments as standards. Structures were confirmed by UV-vis spectroscopy, HPLC retention times and electrospray ionization mass spectrometry. Betaxanthins can be obtained pure, and in sufficient amounts for further studies, which opens up new perspectives in the research and applications of these pigments.

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“…28 Tertiary amines are oxidized to amine oxides, while secondary amines give N-benzoyloxy amines (eq 21). 29 In the presence of a mild base, DBP acts as a very selective oxidizing agent for hydroquinones. 30 Aldehydes and benzylic positions are not affected.…”

Section: Intermolecular Carbon-carbon Bond Forming Reactionsmentioning

confidence: 99%

“…Secondary amines are converted into N-benzyloxy amines (eq 20). 29 An improved protocol 38 for this reaction and an application for synthesis of N 5 -hydroxy-Lornithine 39 have appeared in the literature.…”

Section: Intermolecular Carbon-carbon Bond Forming Reactionsmentioning

confidence: 99%