- SYNTHESIS OF D-GLUCOSE, 2-AMINO-2-DEOXY-D-GLUCOSE HYDROCHLORIDE, AND 2-AMINO-2-DEOXY-D-GLUCOSE HYDROCHLORIDE
-
D-Glucose, 2-amino-2-deoxy-D-glucose hydrochloride, and 2-amino-2-deoxy-D-glucose hydrochloride have been synthesized for use in biosynthetic studies.The two amine hydrochlorides were prepared by a series of reactions involving D-
- Taniguchi, Masao,Nystrom, Robert F.,Rinehart, Kenneth L. Jr.
-
-
Read Online
- Total synthesis of 13C2,15N-imidacloprid with three stable isotopes in the pyridine ring
-
Imidacloprid (IC) is an important crop-protecting insecticide worldwide and commonly used for seed treatment. However, only few data are available on human toxicity of IC. Having in view the metabolic studies at low doses in humans and residue analysis of
- Belov, Vladimir,K?fferlein, Heiko U.
-
p. 126 - 131
(2019/01/24)
-
- Synthesis of 15N-labeled vicinal diamines through N-activated chiral aziridines: Tools for the NMR study of platinum-based anticancer compounds
-
A new method for the synthesis of 15N-labeled chiral β-diamines from a common precursor, either optically pure amino acids or anti-β-amino alcohols, is reported. The two diastereomeric series of vicinal diamines are produced through the nucleophilic ring opening of activated chiral aziridines. 15N was introduced by means of [ 15N]-benzylamine, prepared from 15NH4Cl. The final compounds are highly valuable because [1H-15N] NMR is considered a powerful tool for studying the chemical properties of platinum-based complexes.
- Berger, Gilles,Gelbcke, Michel,Cau?t, Emilie,Luhmer, Michel,Nève, Jean,Dufrasne, Fran?ois
-
p. 545 - 548
(2013/02/23)
-
- NMR studies on the structure of a lithium amide-chiral diether complex for an asymmetric reaction
-
The combination of a chiral diether ligand and a lithium benzyl(trimethylsilyl)amide is a powerful lithium amide reagent for asymmetric conjugate amination of enoate in a toluene solvent. The structure of the chiral diether-lithium amide complex in soluti
- Yamamoto, Yasutomo,Nasu, Hiroyuki,Tomioka, Kiyoshi
-
p. 3836 - 3840
(2013/07/05)
-
- Revealing molecular self-assembly and geometry of non-covalent halogen bonding by solid-state NMR spectroscopy
-
We report a new spectroscopic fingerprint of intermolecular contacts in halogen bond-driven self-assembling aggregates and a precise determination of intermolecular N...I distances in microcrystalline samples. The Royal Society of Chemistry.
- Weingarth, Markus,Raouafi, Noureddine,Jouvelet, Benjamin,Duma, Luminita,Bodenhausen, Geoffrey,Boujlel, Khaled,Schoellhorn, Bernd,Tekely, Piotr
-
supporting information; experimental part
p. 5981 - 5983
(2009/05/06)
-
- Amine-chelated aryllithium reagents - Structure and dynamics
-
Multinuclear NMR studies of five-membered-ring amine chelated aryllithium reagents 2-lithio-N,N-dimethylbenzylamine (1), the diethylamine and diisopropylamino analogues (2, 3), and the o-methoxy analogue (4), isotopically enriched in 6Li and s
- Reich,Goldenberg,Gudmundsson,Sanders,Kulicke,Simon,Guzei
-
p. 8067 - 8079
(2007/10/03)
-
- Efficient methods for the synthesis of [2-15N]guanosine and 2′-deoxy[2-15N]guanosine derivatives
-
The nucleophilic addition-elimination reaction of 2′,3′, 5′-tri-O-acetyl-2-fluoro-O6-[2-(4-nitrophenyl)ethyl]inosine (8) with [15N]benzylamine in the presence of triethylamine afforded the N2-benzyl[2-15N]guanosine derivative (13) in a high yield, which was further convened into the N2-benzoyl[2-15N] guanosine derivative by treatment with ruthenium trichloride and tetrabutylammonium periodate. A similar sequence of reactions of 2′, 3′, 5′-tri-O-acetyl-2-fluoro-O6-[2-(methylthio)ethyl]inosine (9) and the 6-chloro-2-fluoro-9-(β-D-ribofuranosyl)-9H-purine derivative (11), which were respectively prepared from guanosine, with potassium [15N]phthalimide afforded the N2-phthaloyl [2-15N]guanosine derivative (15; 62%) and 9-(2,3,5-tri-O-acetyl-β-D-ribofuranosyl)-6-chloro-2- [15N]phthalimido-9H-purine (17; 64%), respectively. Compounds 15 and 17 were then efficiently converted into 2′,3′,5′-tri-O-acetyl [2-15N]guanosine. The corresponding 2′-deoxy derivatives (16 and 18) were also synthesized through similar procedures.
- Kamaike,Kinoshita,Niwa,Hirose,Suzuki,Ishido
-
-
- 4,4′-Dimethoxytrityl and 4,4′,4″-trimethoxytrityl as protecting groups for amino functions; selectivity for primary amino groups and application in 15N-labelling
-
4,4′-Dimethoxytrityl tetrafluoroborate (DMT+ BF4-) and 4,4′,4″-trimethoxytrityl tetrafluoroborate (TMT+ BF4-) are useful reagents for protecting primary and some secondary amines. Protected amines are obtained either by reaction of DMT+ BF4- or TMT+ BF4- with the amine or by alkylating DMT- or TMT-amine (available from DMT+ BF4- and TMT+ BF4- by treatment with ammonia). Alkylation of DMT- or TMT-amine stops after monoalkylation. Deprotection of the alkylated DMT- and TMT-amine is achieved by treatment with an acid of appropriate molarity (e.g. 0.1 M HCl in 1:1 tetrahydrofuran-water for TMT-amines). The value of the methodology described is illustrated by a synthesis of (15NH2) adenosine. X-Ray molecular structures of one DMT and two TMT derivatives are reported.
- Henderson, Alistair P.,Riseborough, Jane,Bleasdale, Christine,Clegg, William,Elsegood, Mark R. J.,Golding, Bernard T.
-
p. 3407 - 3413
(2007/10/03)
-
- Synthesis of L-histidine specifically labelled with stable isotopes
-
(2'-13C)-, (1'-15N)- and (3'-15N)-L-Histidine were prepared according to a synthetic scheme that allows the 13C or 15N labelling of all carbon and nitrogen positions or any combination of positions.A 1,5-disubstituted imidazole ring was constructed via condensation of tosylmethyl isocyanide with 3-phenylpropenal and subsequent cycloaddition of benzylamine.The imidazole intermediate was converted into 1-benzyl-5-(chloromethyl)-imidazolium chloride which was coupled to a glycine moiety via an enantioselective coupling with the bislactim ether of cyclo-D-valylglycine.Deprotection of the coupling product afforded L-histidine in high optical purity.Syntheses for the isotopically labelled synthons were developed starting from simple, comercially available, highly enriched compounds.The labelled L-histidines were characterized by mass spectrometry and 1H-, 13C- and 15N-NMR spectroscopy.
- Cappon, J. J.,Witters, K. D.,Baart, J.,Verdegem, P. J. E.,Hoek, A. C.,et al.
-
p. 318 - 328
(2007/10/02)
-
- Biosynthetic Studies on the Chitinase Inhibitor, Allosamidin. Origin of the Carbon and Nitrogen Atoms.
-
Allosamidin 1 is a potent insect chitinase inhibitor produced by Streptomyces sp.The biosynthesis of compound 1 was studied by feeding experiments with labelled precursors.Incorporation experiments using - and D-glucose as well as doubly labelled D-glucosamine revealed that each skeleton of N-acetyl-D-allosamine and allosamizoline 2 was derived grom D-glucosamine.Further experiments with L-arginine and -methionine clarified the origin of the dimethylaminooxazoline moiety of compound 2.
- Zhou, Ze-Yang,Sakuda, Shohei,Yamada, Yasuhiro
-
p. 1649 - 1652
(2007/10/02)
-
- Sequence-Specific Cleavage of DNA by N-Bromoacetyldistamycin. Product and Kinetic Analyses
-
N-Bromoacetyldistamycin (BD) is a designed molecule with two structural domains with distinct functions: sequence specific binding to double helical DNA and cleavage of the DNA backbone.An electrophilic bromoacetyl group is appended to the amino and of th
- Baker, Brenda F.,Dervan, Peter B.
-
p. 2700 - 2712
(2007/10/02)
-
- REACTION OF N-BENZYLIDENEPERCHLOROVINYLAMINE WITH PRIMARY AND SECONDARY AMINES
-
When N-benzylideneperchlorovinylamine (C6H5CH=NCCl=CCl2) is reacted with highly basic secondary amines, a rearrangement occurs already under mild conditions, and substituted amino nitriles with the general formula C6H5CH(NR2)CCl2CN, whose structure was rigorously proved by chemical and spectral methods, form unexpectedly.Primary amines react differently with N-benzylideneperchlorovinylamine, and the main reaction products are N-benzylidenealkylamines and dichloroacetonitrile.
- Drach, B. S.,Popovich, T. P.,Kisilenko, A. A.,Kalinin, V. N.,Soifer, G. B.,Gordeev, A. D.
-
p. 1093 - 1099
(2007/10/02)
-