6318-23-6Relevant academic research and scientific papers
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.
The effect of monosaccharides on self-assembly of benzenetricarboxamides
Wang, Jue,Qi, Wenjing,Chen, Guosong
, p. 587 - 591 (2019/01/04)
The interaction between monosaccharides exhibits an important role in the assembly of monosaccharide-containing molecules. In this work, three common monosaccharides, glucose, galactose and mannose, are employed to investigate the effect of monosaccharide on the self-assembly of benzenetricarboxamide (BTA) core-containing molecules. In the presence of monosaccharides, three benzenetricarboxamide derivatives aggregate into different ordered structures. When alanine linkers are introduced to these molecules between the core and the monosacchride, morphologies of three types of monosaccharide BTAs turned to disordered, meanwhile their structures become similar with the increase of the length of alanine linkers, indicating the disappearance of the monosaccharide effects.
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.
Cobalt(III) Complexes of D -Galactosylamine
Lindner, Leonie,Klüfers, Peter
, p. 1869 - 1873 (2015/09/28)
The β-pyranose isomer of D-galactosylamine (1) formed complexes with three different cobalt(III) fragments. Crystals containing the dication [Co(tren)(β-D-Galp1N2H-1-κ2N1,O2)]2+ (3) showed coordination through the anomeric amino group (N1) and the deprotonated hydroxy group (O2) of the 4C1 β-pyranose form, which is also the major isomer of free galactosylamine. The cationic complexes [Co(fac-dien)(β-D-Galp1N2H-1-κ2N1,O2)]2+ (4) and [Co(phen)2(β-D-Galp1N2H-1-κ2N1,O2)]2+ (5) were analysed by NMR spectroscopy and showed the same coordination mode as 3. In terms of available ligand isomers it was shown that 1 exhibits an anomeric equilibrium in solution of both pyranose and both furanose forms as is typical for the parent glycose, galactose.
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.
Carbohydrate-based switch-on molecular sensor for Cu(II) in buffer: Absorption and fluorescence study of the selective recognition of Cu(II) ions by galactosyl derivatives in HEPES buffer
Singhal, Nitin Kumar,Ramanujam, Balaji,Mariappanadar, Vairamani,Rao, Chebrolu Pulla
, p. 3525 - 3528 (2007/10/03)
1-(β-D-Galactopyranosyl-1′-deoxy-1′-iminomethyl) -2-hydroxynaphthalene (L1), possessing an ONO binding core, was found to be selective for Cu2+ ions in N-[2-hydroxyethyl]piperazine- N′-[2-ethanesulfonic acid] buffer, at concentrations ≤580 ppb, at physiological pH by eliciting switch-on behavior, whereas the other ions, viz., Mg2+, Ca2+, Mn2+, Fe2+, Co 2+, Ni2+, Zn2+, and Cd2+, caused no significant change in the fluorescence. Whereas the binding characteristics were ascertained by absorption spectroscopy, the species formed were shown by Q-TOF ES MS.
Synthesis of N-(fluoren-9-ylmethoxycarbonyl)glycopyranosylamine uronic acids
Ying, Laiqiang,Gervay-Hague, Jacquelyn
, p. 367 - 375 (2007/10/03)
The synthesis of 10 N-(fluoren-9-ylmethoxycarbonyl)glycopyranosylamine uronic acids that are amenable to solid-phase synthesis is described. The general synthetic strategy involves initial incorporation of the protected amine, followed by selective TEMPO oxidation of C-6 hydroxyl groups to give the corresponding Fmoc-protected sugar amino acids. Amine incorporation may be accomplished from aminolysis of the free sugar or from glycosyl azide reduction. The reactions can be carried out on multigram scale, providing access to unique monomer units for future incorporation into combinatorial library syntheses.
Improved synthesis of glycosylamines and a straightforward preparation of N-acylglycosylamines as carbohydrate-based detergents
Lubineau, Andre,Auge, Jacques,Drouillat, Bruno
, p. 211 - 220 (2007/10/02)
D-Glucose, D-galactose, lactose, cellobiose, and maltose yield quantitatively the corresponding glycosylamine when treated at 42 deg C for 36 h with a commercial aqueous aolution of ammonia in the presence of one equivalent of ammonium hydrogen carbonate.After lyophilisation, the residue (i.e., the pure glucosylamine) was dissolved in a mixture of ethanol and water, and treated with acyl chlorides to afford in a few minutes N-acylglucosylamines.Micellar proporties of these amophiphilic derivatives were determined.Keywords: Glycosylamines; N-Acylglycosylamines; Non-ionic detergents; Carbohydrate-based detergents; Surfactants
Fmoc-protected, glycosylated asparagines potentially useful as reagents in the solid-phase synthesis of N-glycopeptides
Urge,Otvos Jr.,Lang,Wroblewski,Laczko,Hollosi
, p. 83 - 93 (2007/10/02)
1-Amino 1-deoxy derivatives of unprotected O-β-D-galactopyranosyl-(1 → 3)-2-acetamido-2-deoxy-β-D-glucopyranose, 2-acetamido-2-deoxy-D-galactose, D-galactose, lactose, D-fucose, D-mannose, and 2-deoxy-D-arabino-hexose were prepared and acylated with N-flu
