128960-84-9Relevant academic research and scientific papers
Pseudo-enantiomeric carbohydrate-based N-heterocyclic carbenes as promising chiral ligands for enantiotopic discrimination
Bower, John F.,Galan, M. Carmen,Henderson, Alexander S.
, p. 3012 - 3016 (2020/05/08)
The practical synthesis of carbohydrate-based NHC-Rh complexes bearing C1 or C3 sterically differentiated positions, accessed by glycosylation or SNAr strategies, is reported. These catalysts exhibit pseudo-enantiomeric behaviour in the hydrosilylation of acetophenone. We show that steric bulk at C1 gives preference for (S)-phenyl-1-ethanol, while bulk at C3 leads to the (R)-enantiomer. These results represent the first example of pseudo-enantiomeric carbohydrate-based NHC ligands leading to enantiotopic discrimination.
Synthesis of β-(1→6)-linked N-acetyl-d-glucosamine oligosaccharide substrates and their hydrolysis by Dispersin B
Fekete, Anikó,Borbás, Anikó,Gyémánt, Gy?ngyi,Kandra, Lili,Fazekas, Erika,Ramasubbu, Narayanan,Antus, Sándor
, p. 1445 - 1453 (2011/09/12)
Dispersin B (DspB) from Aggregatibacter actinomycetemcomitans is a β-hexosaminidase exhibiting biofilm detachment activity. A series of β-(1→6)-linked N-acetyl-d-glucosamine thiophenyl glycosides with degree of polymerisation (DP) of 2, 3, 4 and 5 were sy
Conjugates of plumbagin and phenyl-2-amino-1-thioglucoside inhibit MshB, a deacetylase involved in the biosynthesis of mycothiol
Gammon, David W.,Steenkamp, Daniel J.,Mavumengwana, Vuyo,Marakalala, Mohlopheni J.,Mudzunga, Theophilus T.,Hunter, Roger,Munyololo, Muganza
experimental part, p. 2501 - 2514 (2010/06/21)
N-Acetylglucosaminylinositol (GlcNAc-Ins)-deacetylase (MshB) and mycothiol-S-conjugate amidase (Mca), structurally related amidases present in mycobacteria and other Actinomycetes, are involved in the biosynthesis of mycothiol and in the detoxification of
Direct chemical glycosylation with pentenyl- and thioglycoside donors of N-acetylglucosamine
Krag, Jonas,Christiansen, Mira S.,Petersen, Jette G.,Jensen, Henrik H.
experimental part, p. 872 - 879 (2010/06/19)
The use of pentenyl and thiophenyl glycosides of N-acetylglucosamine (GlcNAc) as glycosyl donors for the direct preparation of O-glycosides of GlcNAc promoted by N-iodosuccinimide (NIS) and metal triflates in dichloromethane has been investigated. Both glycosyl acceptors 1-octanol and (-)-menthol resulted in good glycosylation yields for both types of donors with pentenyl glycosides being somewhat superior in terms of yield. Carbohydrate-based acceptors were reacted with a benzylated GlcNAc-pentenyl donor but only provided disaccharides in poor to moderate yields. The results show that a variety of metal triflates are capable of acting as an activator for both NIS and the intermediate oxazoline.
Synthesis and biological activity of aryl S-β-glycosides of 1-thio-N-acetylmuramyl-L-alanyl-D-isoglutamine
Zemlyakov,Tsikalova,Azizova,Chirva,Mulik,Shkalev,Kalyuzhin,Kiselevsky
, p. 223 - 229 (2008/09/21)
Phenyl, p-tolyl, and p-tert-butylphenyl β-1-thio-N- acetylglucosaminides were synthesized by the treatment of thiophenols with peracetate of α-D-glucosaminyl chloride in the presence of triethylamine or under the conditions of phase-transfer catalysis with quaternary ammonium salts. The compounds synthesized were used for obtaining of glycosides of 4,6-O-isopropylidene-N-acetylmuramic acid, which were coupled with L-Ala-D-Glu(NH2)-OBzl and then deprotected to obtain the target aryl β-thioglycosides of N-acetylmuramyl-L-analyl-D-isoglutamine (MDP). The aryl β-thioglycosides of MDP were found to stimulate an antibacterial resistance toward Staphylococcus aureus in mice. The reliable induction of the spontaneous activity of natural killers in the population of blood mononuclear cells was observed only for phenyl β-thio-MDP at a dose of 200 μg/ml.
Diversity-oriented chemical modification of heparin: Identification of charge-reduced N-acyl heparin derivatives having increased selectivity for heparin-binding proteins
Huang, Liusheng,Kerns, Robert J.
, p. 2300 - 2313 (2007/10/03)
The diversity-oriented chemical modification of heparin is shown to afford charge-reduced heparin derivatives that possess increased selectivity for binding heparin-binding proteins. Variable N-desulfonation of heparin was employed to afford heparin fract
Facile Preparation of Glycosyl Donors for Oligosaccharide Synthesis: 2-Azido-2-deoxyhexopyranosyl Building Blocks
Buskas, Therese,Garegg, Per J.,Konradsson, Peter,Maloisel, Jean-Luc
, p. 2187 - 2194 (2007/10/02)
Facile routes to the 2-azido-2-deoxy-1-thioglycosides 6, 7, 15, and 18 and of the 2-azido-2-deoxy-4-pentenoglycoside 11, are described.These are useful intermediates for the synthesis of oligo-saccharides containing α-D-2-amino-2-deoxy (or 2-acetamido-2-d
Dibutylstannylene acetals: Useful intermediates for the regioselective sulfation of glycosides
Guilbert,Davis,Pearce,Aplin,Flitsch
, p. 2163 - 2178 (2007/10/02)
Sulfated mono- and disaccharides were synthesised by a novel sulfation method via regioselective activation of the saccharides to their dibutyltin stannylene acetals, followed by treatment with sulfur trioxide-trimethylamine. This methodology was applied
