Synthesis and properties of new bolaform and macrocyclic galactose-based surfactants obtained by olefin metathesis

Satgé, Céline; Granet, Robert; Verneuil, Bernard; Champavier, Yves; Krausz, Pierre

doi:10.1016/j.carres.2004.03.003

Cited by 36 publications

(24 citation statements)

References 18 publications

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“…The study of interactions between surfactant and sugars [12], in particular cyclodextrins [13], has as objective to improve and increase the application fields of the surfactants. Indeed, the beneficial modification of guest molecular properties after the formation of an inclusion compound leads to a large number of applications related to chemical synthesis and catalysis, pharmaceutical chemistry, and analytical chemistry [14,15].…”

Section: Introductionmentioning

confidence: 99%

NMR diffusometry and conductometry study of the host–guest association between β-cyclodextrin and dodecane 1,12-bis(trimethylammonium bromide)

Cabaleiro-Lago

Nilsson²,

Valente³

et al. 2006

Journal of Colloid and Interface Science

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Section: Introductionmentioning

confidence: 99%

NMR diffusometry and conductometry study of the host–guest association between β-cyclodextrin and dodecane 1,12-bis(trimethylammonium bromide)

Cabaleiro-Lago

Nilsson²,

Valente³

et al. 2006

Journal of Colloid and Interface Science

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“…[30] The reaction of 61 with catalyst 1B gave 62 in 33 % yield. The synthesis of antitumour vaccines in highly clustered modes by RCM is reported by Danishefsky and co-workers (Scheme 11).…”

Section: Macrocyclic Neoglycoconjugatesmentioning

confidence: 99%

Metathesis and Macrocycles with Embedded Carbohydrates

Jarikote

Murphy

2010

Eur J Org Chem

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Macrocycles containing embedded carbohydrates are found in nature. Tricholorin A and G, woodrosin, sophorolipid lactone, cycloviracin B1, glucolipsin A and ipomoeassins A–F are natural products with interesting biological properties. They have inspired synthesis of non‐natural macrocyclic structures which contain embedded carbohydrates. Glycophanes (hybrids of carbohydrates and cyclophanes) were prepared which show potential in host‐guest chemistry and which have been applied as rigid scaffolds for the synthesis of bivalent inhibitors of lectin binding to tumour cells. Macrocyclic neoglycoconjugates have also been prepared. These include macrocyclic neooligoaminodeoxysaccharides which bind to RNA regions containing either asymmetric internal loop or hairpin loop‐stem junctions, and vaccine candidates. Non‐natural macrolides having antibacterial and antifungal activity have been synthesised. Metathesis using Grubbs and Hoyveda‐Grubbs catalysts has been key to the successful generation of these compounds. Herein we review the recent application of metathesis to the synthesis of ipomoeassins A, B and F, glycophanes, neooligoaminodeoxysaccharides,macrolides and other macrocycles with embedded carbohydrates.

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“…The novel pseudomacrocyclic bola-amphiphilic (type B) compounds 303 and 304 have been synthesized (355,356), as have galactose-based (type C) macrocyclic surfactant 305 analogs of archaeobacterial membrane components (356). Compound 305 and the pseudomacrocyclic bolaforms 303 and 304 display interesting new surface tension properties; they are insoluble in water and undergo monolayer compression.…”

Section: Unusual Bolaform Amphiphilesmentioning

confidence: 99%

Astonishing diversity of natural surfactants: 2. Polyether glycosidic ionophores and macrocyclic glycosides

Dembitsky

2005

Lipids

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Polyether glycosidic ionophores and macrocyclic glycosides are of great interest, especially for the medicinal and pharmaceutical industries. These biologically active natural surfactants are good prospects for the future chemical preparation of compounds useful as antibiotics, anticancer agents, or in industry. More than 300 interesting and unusual natural surfactants are described in this review article, including their chemical structures and biological activities.

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Synthesis and properties of new bolaform and macrocyclic galactose-based surfactants obtained by olefin metathesis

Cited by 36 publications

References 18 publications

NMR diffusometry and conductometry study of the host–guest association between β-cyclodextrin and dodecane 1,12-bis(trimethylammonium bromide)

NMR diffusometry and conductometry study of the host–guest association between β-cyclodextrin and dodecane 1,12-bis(trimethylammonium bromide)

Metathesis and Macrocycles with Embedded Carbohydrates

Astonishing diversity of natural surfactants: 2. Polyether glycosidic ionophores and macrocyclic glycosides

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