65870-84-0Relevant academic research and scientific papers
Glycomimetics Targeting Glycosyltransferases: Synthetic, Computational and Structural Studies of Less-Polar Conjugates
Ghirardello, Mattia,De Las Rivas, Matilde,Lacetera, Alessandra,Delso, Ignacio,Lira-Navarrete, Erandi,Tejero, Tomás,Martín-Santamaría, Sonsoles,Hurtado-Guerrero, Ramón,Merino, Pedro
supporting information, p. 7215 - 7224 (2016/05/19)
The Leloir donors are nucleotide sugars essential for a variety of glycosyltransferases (GTs) involved in the transfer of a carbohydrate to an acceptor substrate, typically a protein or an oligosaccharide. A series of less-polar nucleotide sugar analogues derived from uridine have been prepared by replacing one phosphate unit with an alkyl chain. The methodology is based on the radical hydrophosphonylation of alkenes, which allows coupling of allyl glycosyl compounds with a phosphate unit suitable for conjugation to uridine. Two of these compounds, the GalNAc and galactose derivatives, were further tested on a model GT, such as GalNAc-T2 (an important GT widely distributed in human tissues), to probe that both compounds bound in the medium-high micromolar range. The crystal structure of GalNAc-T2 with the galactose derivative traps the enzyme in an inactive form; this suggests that compounds only containing the β-phosphate could be efficient ligands for the enzyme. Computational studies with GalNAc-T2 corroborate these findings and provide further insights into the mechanism of the catalytic cycle of this family of enzymes.
Synthesis of sugar nucleotides by application of phosphoramidites
Gold, Henrik,Van Delft, Pieter,Meeuwenoord, Nico,Codee, Jeroen D. C.,Filippov, Dmitri V.,Eggink, Gerrit,Overkleeft, Herman S.,Van Der Marel, Gijs A.
supporting information; experimental part, p. 9458 - 9460 (2009/04/06)
(Chemical Equation Presented) A new method for the construction of pyrophosphates is reported based on the coupling of a sugar phosphate and a nucleoside phosphoramidite. The in situ formed phosphate-phosphite intermediate was subsequently oxidized with tBuOOH. Three UDP-N-acetylglucosamine derivatives were prepared using this one-pot procedure in good yields.
Phosphotriesters Approach to the Synthesis of Oligonucleotides: A Reappraisal
Reese, Colin B.,Pei-Zhuo, Zhang
, p. 2291 - 2302 (2007/10/02)
The phosphotriester approach to the synthesis of oligodeoxyribo- and oligoribo-nucleotides in solution has been reinvestigated.The efficacy of mesitylene-2-sulfonyl chloride (MSCl) 15a, 2,4,6-triisopropylbenzenesulfonyl chloride (TrisCl) 15b, 4-bromobenzenesulfonyl chloride 15c, naphthalene-1-sulfonyl chloride 39, and 2- and 4-nitrobenzenesulfonyl chlorides 40a and 40b, respectively, as activating agents has been examined.The latter arenesulfonyl chlorides have been used in conjunction with the following nucleophilic catalysts: 1-methylimidazole, 3-nitro-1H-1,2,4-triazole 19, 5-(3-nitrophenyl)-1H-tetrazole 20a, 5-(3,5-dinitrophenyl)-1H-tetrazole 20b, 5-(1-methylimidazol-2-yl)-1H-tetrazole 21, 5--1H-tetrazole 22, 4-ethoxypyridine 1-oxide 14a, 4,6-dinitro-1-hydroxybenzotriazole 29a, 1-hydroxy-4-nitro-6-(trifluoromethyl)benzotriazole 29b, 1-hydroxy-5-phenyltetrazole 30a and 1-hydroxy-5-(3-nitrophenyl)tetrazole 30b.The rates of formation and yields of the fully protected dideoxyribonucleoside and diribonucleoside phosphates 37 and 47, respectively, were determined using various combinations of activating agents and nucleophilic catalysts.Although 2- and 4-nitrobenzenesulfonyl chlorides 40a and 40b, respectively, proved to be the most powerful activating agents, their use in the deoxy-series led to the formation of by-products and hence to unsatisfactory isolated yields of the dideoxyribonucleoside phosphate 37.
SYNTHESIS AND TRANSFORMATION OF DERIVATIVES OF THE N- AND O-GLYCOSIDES OF D-RIBOFURANOIC ACID
Timoshchuk, V. A.
, p. 1198 - 1204 (2007/10/02)
A method was developed for the nonselective oxidation of pyrimidine nucleosides and methyl β-D-ribofuranoside to the uronic acids by successive treatment first with triphenylchloromethane and then with acetic anydride in pyridine, followed by oxidation with chromic anhydride in acetone in the presence of sulfuric acid.The transformations of the obtained uronic acids into anhydronucleosides by the action of phthalimide and into 3',4'-unsaturated nucleosides by the action of 1,5-diazabicycloundec-5-ene are described.
