Synthesis and structural analysis of long chain N-acetyl-N-alkyllactosylamines, a new series of surfactants derived from unprotected lactose

Costes, F.; Ghoul, Mostafa El; Bon, Maryse; Rico‐Lattes, Isabelle; Lattes, Armand

doi:10.1021/la00010a010

Cited by 26 publications

(31 citation statements)

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“…The synthesis of (N dodecylamino) lactitol is described elsewhere [2d], [19] as is (N-acetyl N-dodecyl) lactosylamine [15]. The α-and β-1 N dodecyl-D-maltosides (98%) were supplied by Aldrich and used without further purification.…”

Section: Preparation Of Compoundsmentioning

confidence: 99%

“…-a hydrophilic head consisting of cyclic or acyclic sugar residues based on one or more rings of 5 or 4 carbons bearing different functional groups [9][10][11][12]; -a hydrophobic part; -a linkage between the two parts: an oxygen or sulphur atom [13], a group with various degrees of ionization or polarizability [14,15]. The head and the chain may also be in either the α or β orientation [16].…”

Section: Introductionmentioning

confidence: 99%

“…iii) N-acetyl-N-dodecyl 490 The European Physical Journal E lactosylamine (Ac) (Fig. 1c) where the two sugar residues and the chain are linked with a bulky (N-CO-CH 3 ) group, which also has a hydrophobic group [15]. iv) α-and β-1 N dodecyl-D-maltosides (αM) or (βM) (Fig.…”

Section: Introductionmentioning

confidence: 99%

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Small-angle X-ray diffraction study of the thermotropic and lyotropic phases of five alkyl cyclic and acyclic disaccharides: Influence of the linkage between the hydrophilic and hydrophobic moieties

Auvray

Petipas

Dupuy

et al. 2001

The European Physical Journal E

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We present a comparative study of the thermotropic and lyotropic phases of 5 surfactants with an aliphatic chain of 12 carbon atoms and a cyclic or acyclic sugar head with different linkages between the two moieties. These linkages can concern different chemical groups or different orientations between the head and the chain. The compounds included the α-and β-N dodecyl-D-maltosides, N-dodecylamino-1-deoxylactitol, N-dodecyl lactobionamide and N-acetyl N-dodecyl lactosylamine. The influence of the polar head (with closed-and opened-type sugars) and the linkage with the hydrocarbon chain on the phases obtained by the heating of the anhydrous compounds and after addition of water was studied by X-ray diffraction and optical microscopy. In the anhydrous state, the surfactants were either crystalline or amorphous. On heating, they went through a liquid crystal smectic phase which, in some cases, was preceded by solid-to-solid transitions. On addition of water, the sequence of phases from the micellar phase to the lamellar phase was accounted for in terms of the geometric model of Sadoc and Charvolin. However, with certain surfactants this sequence was not complete, and the domains of existence of phases were altered. PACS. 61.30.Eb Experimental determination of smactic, nematic, cholesteric and other structures -61.10.Nz Single crystal and powder diffraction -64.70.Md Transitions in liquid crystals

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Section: Preparation Of Compoundsmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

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Small-angle X-ray diffraction study of the thermotropic and lyotropic phases of five alkyl cyclic and acyclic disaccharides: Influence of the linkage between the hydrophilic and hydrophobic moieties

Auvray

Petipas

Dupuy

et al. 2001

The European Physical Journal E

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“…In particular, recent fundamental studies have sought to elucidate the behavior of the simple alkylglucosides in the context of other well-characterized nonionic surfactants, namely, those based on poly(ethene oxide) head groups (Ericsson et al, 2004). Interest in surfactants derived from sugars other than glucose has been extended to include other monosaccharides, as well as linear di-, tri-, and tetrasaccharides (Costes et al, 1995;Ferrer et al, 2002;Garofalakis et al, 2000;Kjellin et al, 2001;Plou et al, 2002;Söderberg et al, 1995). The use of branched oligosaccharide head groups has been little explored, presumably due to the difficulties associated with isolating or synthesizing pure compounds.…”

Section: Introductionmentioning

confidence: 99%

Synthesis, preliminary characterization, and application of novel surfactants from highly branched xyloglucan oligosaccharides

Greffe¹,

Bessueille²,

Bulone³

et al. 2004

Glycobiology

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A novel class of nonionic, carbohydrate-based surfactants has been synthesized from the plant polysaccharide xyloglucan. Enzymatic hydrolysis of xyloglucan yielded a series of welldefined, highly branched oligosaccharides that, following reductive amination, were readily conjugated with fatty acids bearing C 8 to C 18 chains under mild conditions. The critical micelle concentration, determined by tensiometry and dye-inclusion measurements, showed a typical dependence on acyl chain length and was sensitive to the degree of galactosylation of the head group. Several compounds from this new group of surfactants, especially those with C 14 and C 16 chains, were useful for the extraction of membrane-bound enzyme markers from different plant cell compartments in catalytically active form.

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“…APGs have also been used in more advanced applications such as the extraction and purification of membrane proteins, which plays a major role in the determination of protein structures and functions [52]. This is because APGs have reduced protein-denaturing properties in comparison to conventional surfactants.…”

Section: Case Study: Alkyl Polyglycosidesmentioning

confidence: 99%

Interactions between Bio-Based Compounds and Cyclodextrins

Medronho¹,

Gonçalves²,

RaquelRodríguez-Solana³

et al. 2018

Cyclodextrin - A Versatile Ingredient

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Bio-based compounds, such as "green" surfactants and phytochemicals, are regarded as future sustainable resources for a vast range of applications in a modern society increasingly demanding economical, social, and environmental awareness. Natural compounds from plants (phytochemicals) are very sought by the pharmaceutical, cosmetic, and food industries. On the other hand, the growing interest in "green" surfactants (e.g., carbohydrate-based) is due to, inter alia, their preparation from renewable raw materials, ready biodegradability, and biocompatibility, among other reasons of fundamental, practical, economical, and environmental orders. Despite the wide range of potential applications of these bio-based compounds, their practical use is still limited due to many reasons such as poor aqueous solubility, volatility, reactivity, etc. Generally, when complexed with cyclodextrins, these biobased compounds enhance considerably their performance and potential applications. Thus, this chapter aims at recalling some general fundamental aspects of phytochemicals and "green" surfactants, such as structure, function, and applications. In addition, their interactions with cyclodextrins are discussed from a physicochemical point of view with special focus on the techniques, mathematic modeling, and thermodynamic parameters (e.g., interactions, stoichiometries, association constants, etc.).

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Synthesis and structural analysis of long chain N-acetyl-N-alkyllactosylamines, a new series of surfactants derived from unprotected lactose

Cited by 26 publications

References 0 publications

Small-angle X-ray diffraction study of the thermotropic and lyotropic phases of five alkyl cyclic and acyclic disaccharides: Influence of the linkage between the hydrophilic and hydrophobic moieties

Small-angle X-ray diffraction study of the thermotropic and lyotropic phases of five alkyl cyclic and acyclic disaccharides: Influence of the linkage between the hydrophilic and hydrophobic moieties

Synthesis, preliminary characterization, and application of novel surfactants from highly branched xyloglucan oligosaccharides

Interactions between Bio-Based Compounds and Cyclodextrins

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