37699-06-2Relevant articles and documents
Click azide-nitrile cycloaddition as a new ligation tool for the synthesis of tetrazole-tethered C-glycosyl α-amino acids
Aldhoun, Mohammad,Massi, Alessandro,Dondoni, Alessandro
experimental part, p. 9565 - 9575 (2009/04/07)
(Chemical Equation Presented) Glycoproteins play a key role in a multitude of biological events in living organisms. Hence, neoglycopeptides obtained from unnatural C-glycosyl α-amino acids can be used as synthetic probes in studies aiming at clarifying the role of the carbohydrate domain in glycoprotein biological activity. A new class of C-glycosyl α-amino acids featuring a nitrogenated heterocycle ring holding the carbohydrate and glycinyl moiety was designed in our laboratory. Having previously prepared isoxazole-, 1,2,3-triazole-, and pyridine-tethered compounds, the family has now been enlarged by a group of newcomers represented by tetrazole derivatives. Two sets of compounds have been prepared, one being constituted of C-galactosyl and C-ribosyl O-tetrazolyl serines while the other contains 5-tetrazolyl cysteine derivatives. In both cases, the synthetic scheme involved a two-step route, the first one being the thermal cycloaddition of a sugar azide with p-toluensulfonyl cyanide (TsCN) to give a 1-substituted 5-sulfonyl tetrazole and the second the replacement of the tosyl group with a serine or cysteine residue. For the high efficiency and operational simplicity, the azide-TsCN cycloaddition appears to be a true click process. Finally, one of the amino acids prepared was incorporated into a tripeptide.
Three-component biginelli cyclocondensation reaction using C-glycosylated substrates. Preparation of a collection of dihydropyrimidinone glycoconjugates and the synthesis of C-glycosylated monastrol analogues
Dondoni, Alessandro,Massi, Alessandro,Sabbatini, Simona,Bertolasi, Valerio
, p. 6979 - 6994 (2007/10/03)
The aldehyde-ketoester-urea cyclocondensation reaction has been revisited using C-glycosylated reagents with the aim of exploring a potential entry to a library of dihydropyrimidinone glycoconjugates. A collection of 13 mono- and bis-C-glycosylated dihydropyrimidinones has been prepared by a parallel synthesis approach using the three-component promoter CuCl/AcOH/BF3· Et2O. The sugar residues have been installed at either N1, C4, or C6 in the monoglycosylated derivatives and at both the C4 and C6 in the bisglycosylated products. The mono- and bisglycosylated products at C4 and C6 were obtained as mixtures of diastereoisomers with good to excellent selectivities due to the asymmetric induction by the sugar residue in the formation of the C4 stereocenter of the dihydropyrimidinone ring. Individual stereoisomers were isolated as pure compounds and their structures assigned with the aid of X-ray crystallography and chiroptical properties. As a demonstration of this new concept in the Biginelli reaction, the synthesis of two C4 epimer monastrol analogues bearing the ribofuranosyl moiety at C6 has been described.
SYNTHESIS OF PHOSPHATE AND PHOSPHATES ISOSTERES OF FURANOSE SUGARS AS POTENTIAL ENZYME INHIBITORS
Maryanoff, Bruce E.,Reitz, Allen B.,Nortey, Samuel O.
, p. 3093 - 3106 (2007/10/02)
Various D-furanose monosaccharides were synthesized as possible inhibitors of the gluconeogenic enzyme fructose 1,6-bisphosphatase.These included sulfamate, phosphoramidate, and epoxy analogues of the natural substrate, fructose 1,6-diphosphate (1), and arabinose and ribose analogues of a natural inhibitor, fructose 2,6-diphosphate (2).NMR studies were conducted to establish the stereochemistry of phosphate displacement at Cl in the synthesis of arabinose 1-phosphate derivatives. β-Ribose 1,5-diphosphate (35b) was prepared with >95 percent stereoselectivity.
