123499-65-0Relevant academic research and scientific papers
Proteinase N-catalysed regioselective esterification of sucrose and other mono- and disaccharides
Potier, Pierre,Bouchu, Alain,Gagnaire, Juliette,Queneau, Yves
, p. 2409 - 2419 (2001)
Crude Proteinase N was used as catalyst for the synthesis of carbohydrate (in particular sucrose) esters by transesterification of activated esters in organic solvents. Polymerisable or amphiphilic sucrose esters (methacrylates and laurates) were obtained
Self-organizing properties of monosubstituted sucrose fatty acid esters: The effects of chain length and unsaturation
Molinier, Valerie,Kouwer, Paul J. J.,Fitremann, Juliette,Bouchu, Alain,Mackenzie, Grahame,Queneau, Yves,Goodby, John W.
, p. 3547 - 3557 (2008/02/04)
Three families of mono-substituted sucrose fatty acid esters were prepared by enzymatic and classical synthetic procedures, and their self-assembly and self-organizational properties were investigated by thermal polarised light microscopy, differential scanning calorimetry and X-ray diffraction. The properties were evaluated as a function of the fatty acid chain length. For the lower homologues of the series columnar liquid-crystalline stacking structures were found, whereas for the higher homologues, lamellar phases predominated. A model for the columnar stacking arrangement, consisting of a unique arrangement of the molecules which could lead to the creation of multiple internal ion channels between the hydrophobic interior and the hydrophilic exterior of the columns, is suggested.
Transesterification of Sucrose in Organic Medium: Study of Acyl Group Migrations
Molinier, Valerie,Wisniewski, Krzysztof,Bouchu, Alain,Fitremann, Juliette,Queneau, Yves
, p. 657 - 669 (2007/10/03)
The tendency of the acyl groups located on the glucose part of sucrose fatty acid esters to undergo intramolecular migrations in organic medium and the regioselectivity of some transesterifications of sucrose were investigated by HPLC, in situ NMR spectroscopy and preparative methods. Extensive acylation on secondary positions of the glucose moiety followed by migrations is general for base catalysed transesterification. The stability of 3- and 6-O-acyl derivatives, two isomers being thermodynamically favored compared to others, was studied in a series of conditions. It is shown that the presence of water catalyzes the migration of the ester at OH-3 towards OH-6 in organic basic medium, whereas the ester at OH-6 appears more stable under either acidic or basic conditions.
A new chemoenzymatic synthesis of 6'-O-acylsucroses
Chauvin,Plusquellec
, p. 3495 - 3498 (2007/10/02)
6'-O-acylsucroses were synthesized for the first time in two steps, including a new chemical selective acylation of free sucrose followed by an enzymatic hydrolysis of the 6-O-acylated by-products.
