A New Route to Carbohydrates Enriched with Oxygen Isotopes

Efficient Synthesis of [2‘-18O]Uridine and Its Incorporation into Oligonucleotides: A New Tool for Mechanistic Study of Nucleotidyl Transfer Reactions by Isotope Effect Analysis

“…As expected, the new compound gave essentially the same 1 H and 13 C NMR spectra as an authentic sample of uridine. In addition, we observed an 18 O-induced 13 C NMR shift of 1.54 Hz upfield for 2‘-C of [2‘- 18 O]uridine, further confirming the position of 18 O 7a 2 Synthesis of [2‘- 18 O]Uridine …”

“…However, this strategy generated arabinofuranosyl derivatives and could not be used to prepare [2‘- 18 O]uridine. Another strategy reported in the literature to prepare 18 O-labeled sugar isotopomers makes use of S N 2-substituted reaction of triflate with 18 O-labeled nucleophiles . Unfortunately, the 2‘-β triflate derivative of uridine failed to undergo the analogous reaction to generate [2‘- 18 O]uridine.…”

Mitsunobu and Related Reactions: Advances and Applications

“…Use of a primary or a saturated achiral alcoholic substrate generally does not pose a problem in the Mitsunobu process, and hence, only a list of compounds wherein it is used is provided here. These include (i) photoresponsive esters with an azobenzene group, using the reaction of the mesogenic alcohols with fumaric acid or maleic acid, (ii) cyclohexyl nitronic ester by starting with cyclohexanol, (iii) polar functional PPV derivatives with ester groups for sensor applications, (iv) capsular polysaccharides, (v) acetylenic esters of 2,3-dibromomaleic acid and isophthalate esters as precursors for dendrimers, (vi) enfumafungin, (vii) buprestin A and B, (viii) cinnamyl monoglyceride, (ix) β-acyl glucuronides, − (x) 17 O-enriched esters of carbohydrates with PhC(O) 17 OH, (xi) bromoacetylation of Wang resin, (xii) (±)-6-myoporol, (xiii) multiple porphyrin arrays through ester linkages, (xiv) 3,5-hexadienyl acrylates, (xv) mono- and di-esters of sucrose with long chain carboxylic acids, (xvi) ( S )-(−)-camphanic acid esters of (hydroxymethyl)pyrroles, (xvii) syn , syn -bicyclo[3.3.0]octyl-2-benzoate, (xviii) an esterification step in the synthesis of syn -enol ethers, (xix) glass forming liquid crystals, (xx) conjugated reactive mesogen 2-methyl-1,4-bis[2-(4-acryloylpropyloxyphenyl)ethenyl]benzene, (xxi) 6,6′-di- O - p -nitrobenzoyl-2,3,4,3′,4′-penta- O -benzyl-1′-methoxymethylsucrose, (xxii) poly(triacetylene) oligomers with ester linkages, (xxiii) β-anomers of bile acid 24-acyl glucuronides, , (xxiv) geodiamolide A (an 18-membered cytotoxic depsipeptide from marine sponges), (xxv) 5′- O -acyl derivatives of nucleosides, , (xxvi) the acetate of ( R )-1-indanol, (xxvii) side chain copolymers containing liquid crystalline and photoactive chromophores, (xxviii) dimethyl-3-((1 Z )-propenyl)cyclopropanecarboxylic acid methyl ester, (xxix) oligothiophene containing photorefractive material with NLO chromophore, and (xxx) 4-flurobenzyl 4-(4-nitrophenyl)butyrate . The structural drawings pertaining to these references are given in the Supporting Information (Table S2).…”

Synthetic methodologies in organic chemistry involving incorporation of [17O] and [18O] isotopes

“…[ 17 O 2 ]‐acetic acid was prepared by incubation of glacial acetic acid with H 2 17 O and HCl at high temperature (Scheme a), by heating a mixture of acetonitrile and H 2 17 O in anhydrous dioxane saturated with dry HCl (Scheme b), and by hydrolysis of acetic acid anhydride with labeled water in the presence of pyridine (Pyr) (Scheme c) . [ 17 O 2 ]‐benzoic acid was prepared by adding a stoichiometric amount of H 2 17 O to benzoyl chloride in Pyr . Hamagan et al ., in order to investigate [ 17 O] NMR spectra in the solid state, prepared [ 17 O]‐labeled benzoic and p ‐methoxybenzoic ( p ‐anisic) acids by acid‐catalyzed exchange in H 2 17 O …”

“…Souza and Lowary presented a simple and efficient method for introduction of oxygen isotopes into carbohydrates, with general applicability. They synthesized a series of [ 17 O]‐enriched monosaccharides and, for the first time, disaccharides.…”