Cycloaddition of Chlorosulfonyl Isocyanate to Sugar Vinyl Ethers

Kałuża, Zbigniew; Abramski, W.; Bełżecki, C.; Grodner, Jacek; Mostowicz, Danuta; Urbanski, R.; Chmielewski, Marek

doi:10.1055/s-1994-22921

Cited by 36 publications

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“…2), both of which are prepared via a one-step procedure. 36 The polymerization is initiated by pentafluorophenol ester 5 or 6 , which have one or two palmitamide chains, respectively. Amphiphiles with DP th ’s of 10 and 20 were prepared by using either 10 or 5 mol% of initiator, respectively.…”

Section: Resultsmentioning

confidence: 99%

Synthesis of bioinspired carbohydrate amphiphiles that promote and inhibit biofilms

et al. 2014

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The synthesis and characterization of a new class of bioinspired carbohydrate amphiphiles that modulate Pseudomonas aeruginosa biofilm formation are reported. The carbohydrate head is an enantiopure poly-amido-saccharide (PAS) prepared by a controlled anionic polymerization of β-lactam monomers derived from either glucose or galactose. The supramolecular assemblies formed by PAS amphiphiles are investigated in solution using fluorescence assays and dynamic light scattering. Dried samples are investigated using X-ray, infrared spectroscopy, and transmission electron microscopy. Additionally, the amphiphiles are evaluated for their ability to modulate biofilm formation by the Gram-negative bacterium Pseudomonas aeruginosa. Remarkably, from a library of eight amphiphiles, we identify a structure that promotes biofilm formation and two structures that inhibit biofilm formation. Using biological assays and electron microscopy, we relate the chemical structure of the amphiphiles to the observed activity. Materials that modulate the formation of biofilms by bacteria are important both as research tools for microbiologists to study the process of biofilm formation and for their potential to provide new drug candidates for treating biofilm-associated infections.

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Section: Resultsmentioning

confidence: 99%

Synthesis of bioinspired carbohydrate amphiphiles that promote and inhibit biofilms

et al. 2014

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“…[12] The [2ϩ2] cycloaddition of chlorosulfonyl isocyanate to 9, 10, 19 and 20 was carried out in toluene solution in the presence of pulverised anhydrous sodium carbonate. [13] The chlorosulfonyl substituent was removed from the resultant cycloadduct's nitrogen atoms by the Red-Al reduction. [14] Scheme 1…”

Section: Synthesis Of Alkoxyallenes Cycloaddition and Formation Of Cmentioning

confidence: 99%

“…The cycloadditions of CSI to 47 and 46 were carried out following our standard procedure [13] to afford corresponding mixtures of the β-lactams 48/49 and 54/55 in ratios 1:1 and 1.65:1, respectively. Subsequent desilylation followed by the tosylation and intramolecular alkylation at the nitrogen atom led to the corresponding cephams 58/59 and 60/61 which were separated into pure components by chromatography.…”

Section: Synthesis Of Alkoxyallenes Cycloaddition and Formation Of Cmentioning

confidence: 99%

“…[21] This program, utilising a full relaxation matrix of the spin system under consideration, allows calculation of steady state NOE enhancements using specific correlation times for individual CϪH vectors derived from 13 C-T 1 measurements. The calibration of NOEs can be accomplished by the ''external relaxation'' parameter, ρ ext , applied to isolated geminal protons serving as a reference within a molecule.…”

Section: Noe Measurementsmentioning

confidence: 99%

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Stereochemistry of the [2+2] Cycloaddition of Chlorosulfonyl Isocyanate to Chiral Alkoxyallenes Derived from 1,3‐Alkylidene‐L‐erythritol and ‐D‐threitol

et al. 2005

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The [2+2] cycloaddition of chlorosulfonyl isocyanate to alkoxyallenes derived from ethylidene and benzylidene erythritols and threitols proceeds with a moderate asymmetric induction in the case of the erythritols and with a very low induction in the case of threitols. This indicates that the erythritol derivatives may exist in solution in one predominant conformation while the threitol derivatives behave as a conformational ensemble. The conformations of alkoxyallenes were studied with variety of NMR techniques as well as using ab initio

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“…Using para -nitrobenzoyl chloride as the initiator, the anionic ring-opening polymerization 11 of monomer 1 12 was performed at three different initiator loadings (4, 2, and 1 mol%) to prepare a series of polymers of increasing degrees of polymerization, P1' 25 , P1' 50 , and P1' 100 (DP th = 25, 50, 100, respectively) (Scheme 2). Complete consumption of the monomer was observed with initiator loadings of 4 and 2 mol%.…”

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confidence: 99%

Synthetic Enantiopure Carbohydrate Polymers That Are Highly Soluble in Water and Noncytotoxic

2013

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The first synthesis of poly-amido-saccharides (PASs) from a galactose(gal)-derived β-lactam sugar monomer is reported. The polymers are prepared using a controlled anionic ring-opening polymerization and characterized by NMR, optical rotation, IR, and GPC. Galactose-derived PASs display high solubility in aqueous solutions and are noncytotoxic to HepG2, CHO, and HeLa cell lines. To evaluate whether gal-derived PASs are recognized by the gal-specific lectin present on human hepatocytes, cellular uptake of rhodamine-labeled polymers is assessed using flow cytometry and fluorescence microscopy. Based on these results, the polymers are taken into cells via endocytosis that is not dependent on the gal-specific receptor on hepatocytes. Neutral, hydrophilic polymers, such as gal-derived PASs, are desirable materials for a range of biomedical applications, such as drug delivery, surface passivation, and hydrogel formation.

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Cycloaddition of Chlorosulfonyl Isocyanate to Sugar Vinyl Ethers

Cited by 36 publications

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Synthesis of bioinspired carbohydrate amphiphiles that promote and inhibit biofilms

Synthesis of bioinspired carbohydrate amphiphiles that promote and inhibit biofilms

Stereochemistry of the [2+2] Cycloaddition of Chlorosulfonyl Isocyanate to Chiral Alkoxyallenes Derived from 1,3‐Alkylidene‐L‐erythritol and ‐D‐threitol

Synthetic Enantiopure Carbohydrate Polymers That Are Highly Soluble in Water and Noncytotoxic

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