2012
DOI: 10.1016/j.carres.2011.10.036
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Efficient double glycoconjugation to naturalize high molecular weight disperse dyes

Abstract: a b s t r a c tCommercially available Disperse Orange 29 (1a) and Disperse Red 1 (2a) were elaborated to glycoconjugated species, following a new version of a previously-described 'naturalisation' procedure. Glutamic acid was chosen to achieve a double glycoconjugation, which is essential to give to the original disperse dye a water solubility suitable for reaching optimal dyeing conditions. UV-vis plot of the 'naturalised' species showed negligible differences when compared to those of the commercial dyes.Ó 2… Show more

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Cited by 22 publications
(17 citation statements)
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“…Deprotonation of the phenol group of 1 (K 2 CO 3 was typically used) may be responsible for an intermediate hampering the catalytic cycle of the process. Therefore, we reckoned to circumvent this issue by analysing the chemical behaviour of compounds 2 and 3 (Scheme ) as key intermediates in the synthesis of naturalised dyes ,…”
Section: Resultsmentioning
confidence: 99%
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“…Deprotonation of the phenol group of 1 (K 2 CO 3 was typically used) may be responsible for an intermediate hampering the catalytic cycle of the process. Therefore, we reckoned to circumvent this issue by analysing the chemical behaviour of compounds 2 and 3 (Scheme ) as key intermediates in the synthesis of naturalised dyes ,…”
Section: Resultsmentioning
confidence: 99%
“…They possess good fastness properties and hue intensity, that are key parameters in the search of the ideal colorant . Recently, we have disclosed a new class of naturalised dyes, that are glycoconjugate derivatives of chromophores, including anthraquinones ,. In this relevant case, anthraquinones bearing a phenolic group were O‐alkylated, to introduce an ethanoic acid C‐substituent suitable for dye “naturalization” .…”
Section: Introductionmentioning
confidence: 99%
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“…In particular, the known yellow azo dye (8) [12] and the commercial Disperse Red 13 (9) were used in the preparation of GADs following route A (Scheme 2) while derivative 10, prepared by succinylation of commercial alcoholic azo dye Disperse Red 1, [4] was employed in the condensation reaction with the aminosugar derivatives 4 [10] and 5 [8] (route B).…”
Section: Resultsmentioning
confidence: 99%
“…The doubleconjugation procedure required a preliminary insertion of a malonate spacer followed by condensation with two 6 - amino-6 -deoxylactose units [8]. Also, glutamic acid was used as the additional spacer in order to allow the doubleconjugation [9]. Presented here is an extension of our previous results, namely, the synthesis of the third generation of naturalized GADs by conjugation of low molecular weight monoazo dyes with either 6-amino-6-deoxy-d-galactose or 6 -amino-6 -deoxylactose through mixed amido-ester connections (3).…”
Section: Introductionmentioning
confidence: 99%