cas 7240-90-6, 5-Bromo-4-chloro-3-indolyl-beta-D-galactoside

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Synthesis of precipitating chromogenic/fluorogenic β-glucosidase/β-galactosidase substrates by a new method and their application in the visual detection of foodborne pathogenic bacteria
We developed a new efficient method for the synthesis of important indoxyl glycoside substrates for β-glucosidase and β-galactosidase by using 1-acetylindol-3-ones as intermediates. This method was used to synthesise novel precipitating fluorogenic substrates for β-glucosidase based on 2-(benzothiazol-2′-yl)-phenols. We also assessed the application of these substrates in the detection of foodborne pathogenic bacteria.
Wei, Xianhu,Wu, Qingping,Zhang, Jumei,Zhang, Youxiong,Guo, Weipeng,Chen, Moutong,Gu, Qihui,Cai, Zhihe,Lu, Mianfei
p. 103 - 106
(2016/12/27)

Synthesis method of glucoside based on indoxyl derivative and 2-(benzothiazol-2'-yl)phenol derivative
The invention discloses a synthesis method of glucoside based on an indoxyl derivative and a 2-(benzothiazol-2'-yl)phenol derivative. The general formula of a synthetic equation of the synthesis method is as shown in the description; the Ar-OH represents aromatic phenol or a ketonic compound thereof, and is used as a glycosyl receptor in a glycosylation reaction; the G-X represents halogenated sugar, and is used as a glycosyl donor in the glycosylation reaction. According to the synthesis method of the glucoside based on the indoxyl derivative and the 2-(benzothiazol-2'-yl)phenol derivative, a 1-acetylindolin-3-one derivative is selected and used as an intermediate; a novel synthesis method is researched and developed to prepare the glucoside based on the indoxyl derivative; a novel glycosidase fluorescence probe based on a BTP ((2-benzothiazol-2'-yl)phenyl) derivative is synthesized by applying the method; meanwhile, the application effects of the glucoside based on the indoxyl derivative and the glycosidase fluorescence probe are investigated. The glucoside based on the indoxyl derivative and the 2-(benzothiazol-2'-yl)phenol derivative can be used as glycosidase substrates, and is used for the positioning analytic detection and screening on the corresponding glycosidase, a microorganism using the corresponding glycosidase as a characteristic target, and the like.
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(2017/08/28)

Indoxylic acid esters as convenient intermediates towards indoxyl glycosides
Indoxylic acid methyl and allyl esters with varied halide-substitution patterns were obtained in excellent yields using a scalable route. Phase-transfer glycosylation of these key intermediates was carried out with various glycosyl halides. Subsequent mild silver-mediated decarboxylation followed by Zemplen deacetylation led to indoxyl glycosides in good overall yields. Indoxyl glycosides are well-established and widely used tools for enzyme screening and enzyme-activity monitoring. In the past, their synthesis has been difficult, so this new approach has led to a variety of useful structures. Indoxyl glycosides with varied halide-substitution patterns were synthesized using indoxylic acid esters as key intermediates. Glycosylation under phase-transfer conditions, ester cleavage, and mild decarboxylation led to the indoxyl glycosides in good yields. This approach enables access to a number of different indoxyl compounds. Copyright
Boettcher, Stephan,Thiem, Joachim
p. 564 - 574
(2014/02/14)

Enzymatic synthesis of colorimetric substrates to determine α-2,3- and α-2,6-specific neuraminidase activity
Glycoconjugates containing either terminal α-2,3- or α-2,6-Neu5Ac-Gal disaccharides are found on cell surfaces of many animal glycans. Each linkage can be specifically recognized by lectins and enzymes such as neuraminidases. Here we describe a one-step enzymatic synthesis of two colorimetric substrates that allow for fast distinction of specific neuraminidase activity. The Royal Society of Chemistry 2013.
Reyes Martinez, Juana Elizabeth,Sardzik, Robert,Voglmeir, Josef,Flitsch, Sabine L.
p. 21335 - 21338
(2013/11/06)

Novel alizarin-based chromogenic substrates, their uses and composition containing same
The invention concerns a novel chromogenic substrate based on Alizarin. The invention also concerns the uses to which this substrate can be put, and a formulation containing such a substrate. It consists therefore of a substrate to detect the presence of an enzyme activity, with the following general formula: in which: the two ketone groups of the central ring can be replaced by one group R11 (in the upper position), and by OH (in the lower position). R1 is a target part or H, and R2 is a target part or H, with at least one out of R1 and R2 being a target part, R3 is H, SO3H, Cl, Br, F, I, NO2, NH2, NR9R10, or an Acylamino Aminoaryl or Aminoacylamino group of the type NHCOX, with X being an Alkyl, Aryl or Aralkyl group or an a-amino acid residue such as Alanine, R4 is H, SO3H, Cl, Br, F, I, NO2, NH2, NR9R10, OH or an Acylamino Aminoaryl or Aminoacylamino group of the type NHCOX, with X being an Alkyl, Aryl or Aralkyl group or an α-amino acid such as Alanine, according to a modification, R3 and R4 form bonds with one another to create a ring with at least five sides, and preferably six sides. R5, R6, R7 and R8 each consist of one of the following atoms or groups of atoms: H, a halogen (particularly Cl or Br), OH, SO3H, or an Alkyl or Alkoxy group, and R9 a R10 are independently a Methyl, Alkyl, Aryl, Aralkyl group, or one (either R9 or R10) is a ring structure (Piperidine, Pyrrolidine, Morpholine, etc.) with the other (either R10 or R9) being a Hydrogen atom. The invention is particularly applicable in the field of diagnosis.
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(2008/06/13)