123706-60-5Relevant academic research and scientific papers
Evaluating N-benzylgalactonoamidines as putative transition state analogs for β-galactoside hydrolysis
Fan, Qiu-Hua,Striegler, Susanne,Langston, Rebekah G.,Barnett, James D.
, p. 2792 - 2800 (2014/05/06)
Experimental evidence is provided for p-methylbenzyl-d-galactonoamidine to function as a true transition state analog for the enzymatic hydrolysis of aryl-β-d-galactopyranosides by β-galactosidase (A. oryzae). The compound exhibits inhibition constants in the low nanomolar concentration range (12-56 nM) for a selection of substrates. Along these lines, a streamlined synthetic method based on phase-transfer catalysis was optimized to afford the required variety of new aryl-β-d-galactopyranosides. Last, the stability of the galactonoamidines under the assay conditions was confirmed. This journal is the Partner Organisations 2014.
Synthesis and evaluation of glycosyl donors with novel leaving groups for transglycosylations employing β-galactosidase from bovine testes
Kroeger, Lars,Thiem, Joachim
, p. 467 - 481 (2008/03/13)
Novel aryl β-d-galactopyranosides were synthesized employing phase-transfer catalysis, and assayed as potential galactose donors in the presence of β-galactosidase from bovine testes using pNP-Gal as a reference. The aglycones were represented mainly by nitrophenols containing halogens, hydroxymethyl, aldehyde, carboxyl, ester or amino functions. An unusual intermolecular acetyl migration onto the benzylic alcohol group was observed during galactosylation of hydroxymethylnitrophenols. Pyridyl glycosides were obtained by reaction with the corresponding silver pyridinolates. Glycosides of halo-, hydroxymethyl- or methoxycarbonyl-nitrophenols as leaving groups gave virtually the same yields of transglycosylation products. A minor increase was achieved with nitrosalicylaldehyde as leaving group, whereas carboxy or amino derivatives gave very low or no yield of the transglycosylation product. Commercially available donors such as resorufinyl and 4-methylumbelliferyl β-d-galactopyranosides exhibited a lower transglycosylation potential than these novel pNP-Gal derivatives.
Synthesis, characterization, kinetic parameters, and diagnostic application of a sensitive colorimetric substrate for β-galactosidase (2-chloro-4-nitrophenyl-β-D-galactopyranoside)
Hwang,Scott
, p. 284 - 293 (2007/10/02)
The synthesis and characterization of 2-chloro-4-nitrophenyl β-D-galactopyranoside, an improved chromogenic substrate for β-galactosidase, is described. The important kinetic parameters (Km, Vmax and Kp) for this substrate were compared with those of other substrates. The diagnostic utility of this substrate in a digoxin liposome immunoassay is discussed. The new substrate offers at least four times the sensitivity enhancement as that with ortho-nitrophenyl β-D-galactopyranoside in the assays for β-galactosidase. This substrate should find use in enzyme immunoassays where βgalactosidase is used as a label. Copyright
Substrates for β-galactosidase
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, (2008/06/13)
A substrate for β-galactosidase having the general formula STR1 wherein X is halogen; Y is halogen, lower alkyl or hydrogen; W is lower alkyl or hydrogen; and Z is nitro.
