7240-90-6Relevant articles and documents
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
Wei, Xianhu,Wu, Qingping,Zhang, Jumei,Zhang, Youxiong,Guo, Weipeng,Chen, Moutong,Gu, Qihui,Cai, Zhihe,Lu, Mianfei
, p. 103 - 106 (2016/12/27)
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.
Synthesis method of glucoside based on indoxyl derivative and 2-(benzothiazol-2'-yl)phenol derivative
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, (2017/08/28)
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.
Indoxylic acid esters as convenient intermediates towards indoxyl glycosides
Boettcher, Stephan,Thiem, Joachim
, p. 564 - 574 (2014/02/14)
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
Enzymatic synthesis of colorimetric substrates to determine α-2,3- and α-2,6-specific neuraminidase activity
Reyes Martinez, Juana Elizabeth,Sardzik, Robert,Voglmeir, Josef,Flitsch, Sabine L.
, p. 21335 - 21338 (2013/11/06)
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.
Novel alizarin-based chromogenic substrates, their uses and composition containing same
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, (2008/06/13)
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.
