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Chadi Khoury François Le Goffic Marie‐Noëlle Rager 《Journal of carbohydrate chemistry》2013,32(7):395-409
The synthesis of 2‐acetamido‐2‐deoxy‐6‐O‐octanoyl‐D‐glucono‐1,5‐lactone 9 and 2‐acetamido‐2‐deoxy‐6‐O‐octanoyl‐α‐D‐glucopyranose 7 from 2‐acetamido‐2‐deoxy‐α‐D‐glucopyranose is reported. For both targets, the key intermediate was allyl 2‐acetamido‐3,4‐di‐O‐benzyl‐2‐deoxy‐6‐O‐octanoyl‐α‐D‐glucopyranoside 5. Surface tension measurements (critical micellar concentration of 22.3 mM and 5 mM for 9 and 7, respectively) showed up the surface activity of both compounds, while enzyme inhibition assays indicated that 9 could inhibit bovine β‐N‐acetylglucosaminidase (Ki=6.5 µM) but not Serratia marcescens chitobiase nor hen egg‐white lysozyme. Moreover, 7 was shown to induce chitinase production of S. marcescens and to be readily metabolized by these bacteria. 相似文献
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IntroductionSinceSchifbaseanditsmetalcomplexesareofantibacterialandanticancerbioactivities,theyhavebeenaresearchsubjectofmuch... 相似文献
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Dimethylmaleoyl (DMM) moiety has become an important amine protective group in sugar chemistry. We disclose herein that DMM-containing
D-glucosamine analogues, because of their electrophilic nature, are prone to reactions with strong nucleophiles, such as hydrazine,
resulting in a set of undesired side products that are difficult to detect, yet proved to be problematic for organic synthesis. 相似文献
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Stacy P. Ali 《Journal of carbohydrate chemistry》2013,32(4):185-196
The order of reactivity of OH and NH groups of glucosamine hydrochloride (GlcNH2.HCl) and N-acetyl glucosamine (GlcNAc) toward benzylation with NaH/BnBr in DMF was investigated. For GlcNH2.HCl, benzyl groups were introduced in the order of N-Bn > N-Bn2 > 1-O-Bn > 6-O-Bn > 4-O-Bn > 3-O-Bn; for GlcNAc, benzyl groups were introduced in the order of 1-O-Bn > 6-O-Bn > 4-O-Bn > 3-O-Bn > N-Bn. A range of partially benzylated 2-N,N′-dibenzyl glucopyranosides and GlcNAc derivatives were obtained in a single step. 相似文献
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Waêl Moukarzel Jean‐Daniel Marty Dietmar Appelhans Monique Mauzac Juliette Fitremann 《Journal of polymer science. Part A, Polymer chemistry》2013,51(17):3607-3618
A straightforward method for the preparation of polysiloxanes grafted with carbohydrate side groups is described. Two kinds of backbones have been functionalized, namely one‐dimensional, linear polysiloxanes, and hyperbranched poly(siloxysilane)s based on cyclotetrasiloxanes. The method enables us to keep a good integrity of the polysiloxane backbone. The introduction of intermediate activated esters as side groups on the polysiloxane backbone ensures a complete homogeneity of the reaction medium during sugar grafting in dimethyl sulfoxide, and consequently an easy grafting with the unprotected amino sugar. Solubility of the resulting polysiloxanes has been tested in various solvents. The sugar‐grafted polysiloxanes are good candidates for applications such as silicone formulations, hydrophilic silicone elastomers, interactions with metallic nanoparticles, and suspension stabilization, or as starting point for the design of more complex polysiloxanes for molecular recognition. © 2013 Wiley Periodicals, Inc. J. Polym. Sci., Part A: Polym. Chem. 2013, 51, 3607–3618 相似文献
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《Journal of mass spectrometry : JMS》2017,52(12):823-829
Ion mobility spectrometry (IMS) is an analytical technique that separates gas‐phase ions drifting under an electric field according to their size to charge ratio. We used electrospray ionization‐drift tube IMS coupled to quadrupole mass spectrometry to measure the mobilities of glucosamine (GH+) and caffeine (CH+) ions in pure nitrogen or when the shift reagent (SR) 2‐butanol was introduced in the drift gas at 6.9 mmol m−3. Binding energies of 2‐butanol‐ion adducts were calculated using Gaussian 09 at the CAMB3LYP/6‐311++G(d,p) level of theory. The mobility shifts with the introduction of 2‐butanol in the drift gas were −2.4% (GH+) and −1.7% (CH+) and were due to clustering of GH+ and CH+ with 2‐butanol. The formation of GBH+ was favored over that of CBH+ because GBH+ formed more stable hydrogen bonds (83.3 kJ/mol) than CBH+ (81.7 kJ/mol) for the reason that the positive charge on CH+ is less sterically available than on GH+ and the charge is stabilized by resonance in CH+. These results are a confirmation of the arguments used to explain the drift behavior of these ions when ethyl lactate SR was used (Bull Kor Chem Soc 2014, 1023–1028). This study is a step forward to predict IMS separations of overlapping peaks in IMS spectra, simplifying a procedure that is trial and error by now. 相似文献
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《Magnetic resonance in chemistry : MRC》2002,40(3):231-236
The assignments of 1H and 13C NMR chemical shifts together with x‐ray diffraction data for synthesized diosgenyl 3,4,6‐tri‐O‐acetyl‐2‐deoxy‐2‐tetrachlorophthalimido‐β‐D ‐glucopyranoside are described. The structure of this glycoside was established by using homo‐ and heteronuclear two‐dimensional NMR techniques. X‐ray diffraction data for this compound are also reported. Copyright © 2002 John Wiley & Sons, Ltd. 相似文献
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Qi Chen Qian‐Yi Cheng Yan‐Chao Zhao Bao‐Hang Han 《Macromolecular rapid communications》2009,30(19):1651-1655
Novel glucosamine hydrochloride functionalized water‐soluble conjugated polyfluorene was easily synthesized through Cu(I)‐catalyzed azide/alkyne “click” ligation and Suzuki coupling polymerization. The water‐solubility and biocompatibility of the polymer were improved after grafting glucosamine hydrochloride to the side chains of the conjugated polymer. As a fluorescent model system of chitosan, its interaction with single‐stranded DNA was studied by spectrofluorometric titration.
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A liquid chromatography-electrospray ionization mass spectrometry (LC-ESI-MS) method was developed and validated for the assay of glucosamine sulfate in human plasma. Plasma proteins were precipitated by acetonitrile, followed by vortex mixing and centrifugation. The supernatant was transferred and derivatized with phenyl iso-thiocyanate in acetonitrile at 60 degrees C for 40 min. Chromatographic separation was performed on a C(18) column (Inertsil ODS-3 150 x 2.1 mm i.d., 5 microm, JP) with a mobile phase gradient consisting of 0.2% acetic acid (aqueous) and methanol at a flow-rate of 0.3 mL/min. MS detection using electrospray ionization (ESI) as an interface was used in single ion monitoring mode to determine positive ions at m/z 297. This method was shown to be selective and sensitive for glucosamine sulfate. The limit of detection was 35 ng/mL for glucosamine sulfate in plasma and the linear range was 0.1-20 microg/mL in plasma with a correlation coefficient (r) of 0.9991. The relative standard deviations (RSDs) of intra-day and inter-day assays were 8.7-11.4 and 9.8-12.6%, respectively. Extraction recoveries of glucosamine sulfate in plasma were greater than 73%. This method proved to be simple, reproducible and feasible for pharmacokinetic studies of glucosamine sulfate in healthy volunteers after a single oral administration (1500 mg). The pharmacokinetic parameters and relative bioavailabilities were investigated for both domestic glucosamine sulfate tablet and capsule preparations compared with an imported capsule product. 相似文献