6318-23-6Relevant articles and documents
A convenient approach for solution-phase synthesis of water-soluble galactoside libraries
Hong, Feng,Fan, Erkang
, p. 6073 - 6076 (2001)
A convenient approach for the solution-phase synthesis of water-soluble galactoside libraries through tributylphosphine promoted reaction of azido compounds with carboxylic acids is described.
Development of photoswitchable inhibitors for β-galactosidase
Rustler, Karin,Mickert, Matthias J.,Nazet, Julian,Merkl, Rainer,Gorris, Hans H.,K?nig, Burkhard
supporting information, p. 7430 - 7437 (2018/10/24)
Azobenzenes are of particular interest as a photochromic scaffold for biological applications because of their high fatigue resistance, their large geometrical change between extended (trans) and bent (cis) isomer, and their diverse synthetic accessibility. Despite their wide-spread use, there is no reported photochromic inhibitor of the well-investigated enzyme β-galactosidase, which plays an important role for biochemistry and single molecule studies. Herein, we report the synthesis of photochromic competitive β-galactosidase inhibitors based on the molecular structure of 2-phenylethyl β-d-thiogalactoside (PETG) and 1-amino-1-deoxy-β-d-galactose (β-d-galactosylamine). The thermally highly stable PETG-based azobenzenes show excellent photochromic properties in polar solvents and moderate to high photostationary states (PSS). The optimized compound 37 is a strong competitive inhibitior of β-galactosidase from Escherichia coli and its inhibition constant (Ki) changes between 60 nM and 290 nM upon irradiation with light. Additional docking experiments supported the observed structure-activity relationship.
Experimental and computational studies of the recognition of amino acids by galactosyl-imine and -amine derivatives: An attempt to understand the lectin-carbohydrate interactions
Ahuja, Rohit,Singhal, Nitin K.,Ramanujam, Balaji,Ravikumar, Maddula,Rao, Chebrolu P.
, p. 3430 - 3442 (2008/02/03)
(Chemical Equation Presented) A galactosyl-naphthyl-imine-based derivative, 1-(β-D-galactopyranosyl-1′-deoxy-1′-iminomethyl)-2- hydroxynaphthalene (GNI), and a galactosyl-naphthyl-amine-based derivative, 1-(galactopyranosyl-1′-deoxy-1′-aminomethyl)-2-hydroxynaphthalene (GNA), possessing an ONO binding core were studied for their recognition of naturally occurring amino acids using fluorescence and absorption spectroscopy, and the corresponding association constants were derived for the complexes formed. The complexes formed between GNI/GNA and amino acids were supported by electrospray ionization mass spectrometry (ESI/MS). The structures of the complexes were optimized by computational studies using density functional theory, and stabilization energies were computed for the complexes to substantiate the interactions present between GNI/GNA and amino acid. The interactions were found to be primarily hydrogen bonding in nature. These interactions are reminiscent of those present in the lectin-carbohydrate and glycosidase substrate. Thus, the carbohydrate moiety present in GNI shows high specificity toward the -COOH group of the amino acid, which may be relevant to such interactions present between the carbohydrates and the polypeptides.