Hybrid Double-Chain Maltose-Based Detergents: Synthesis and Colloidal and Biochemical Evaluation

Abstract

Four hybrid double-chain surfactants with a maltose polar head were synthesized. The apolar domain consists of a hydrogenated chain, and a partially fluorinated chain made of a propyl hydrogenated spacer terminated by a perfluorinated core of various lengths. Their water solubility was found to be lower than 1 g/L irrespective of the length of both chains. The self-assembling properties of pure hybrids in water were studied by dynamic light scattering and transmission electron microscopy, which revealed the formation of two populations of aggregates with diameters of 8–50 nm and 80–300 nm. When mixed with the classical detergent n-dodecylmaltoside (DDM), the four hybrids were well soluble and formed small mixed micelles. DDM/hybrid mixtures were further evaluated for the extraction of the full-length, wild-type human GPCR adenosine receptor (A2AR), and the bacterial transporter AcrB. The solubilization of A2AR showed extraction efficiencies ranging from 40 to 70%, while that of AcrB reached 60–90%. Finally, three of the hybrids exhibited significant thermostabilization when present as additives. The derivative with a C12-hydrogenated chain and a C4F9-fluorinated chain emerged as the most potent additive exhibiting both good extraction yields of A2AR and AcrB and thermostabilization of A2AR by ∼7 °C.

Detergent‐Like Polymerizable Monomers: Synthesis, Physicochemical, and Biochemical Characterization

“…Compounds 8a–b were synthesized following an eight‐step synthetic route starting from 1,2‐dodecanediol (Scheme ). Selective protection of the primary alcohol group was achieved using Et 3 N and 1.2 equivalent of trityl chloride as previously reported . Mesylation of the secondary alcohol group followed by nucleophilic substitution in the presence of NaN 3 afforded compound 3 in good yield (65 % in three steps).…”

Hybrid Fluorocarbon–Hydrocarbon Surfactants: Synthesis and Colloidal Characterization

“…Catalytic hydrogenolysis of 1 followed by the coupling of 2H,2H,3H,3H-perfluorononanoic acid led to compound 3 in 77% yield. Insertion of the fluorocarbon chain was confirmed by 19 F NMR and 1 H NMR with the appearance of a multiplet at 2.57−2.44 ppm, corresponding to both −CH 2 in α and β positions of the fluorinated tail. Removal of the tBu protecting group was achieved under acidic conditions, and the resulting alcohol 4 was converted into its activated mesyl form in DCM at −10 °C for 1 h, leading to the mesyl derivative 5 without any purification.…”

“…Melting points were determined using an Electrotherma IA9100 apparatus. NMR spectra were recorded on a Bruker AC400 at 400, 100, and 375 MHz for 1 H, 13 C, and 19 F NMR analyses, respectively. Chemical shifts are given in ppm relative to the solvent residual peak as a heteronuclear reference for 1 H and 13 C. Abbreviations used for signal patterns are as followed: bs, broad singlet; s, singlet; d, doublet; t, triplet; q, quartet; m, multiplet; and dd, doublet of doublet.…”

“…13 C{ 1 H} NMR (100 MHz, CDCl 3 ) δ 171.2; 168.1; 70.9; 68.7; 39.4; 31.9; 29.5; 29.3; 29.3; 27.0; 22.7; 19.8; 14.2. 19 tert-Butyl-N-[1-(methylsulfonyloxy)-2-(hexylamino)-2-oxoethyl]carbamate (9a). Characterization data for compound 8a has already been reported in the literature.…”

“…14 To explore the impact of the nature of the headgroup, the development of nonionic F−H surfactants was also investigated by Miyazawa. 15 Since then, a few F−H surfactants bearing a nonionic headgroup have been synthetized such as Janus dendrimers, 16 tertiary amine F−H derivatives, 17,18 or maltose-based 19 and diglucosylated 20 F−H surfactants. The two last series were successfully synthetized in our group and used as additives for the extraction and stabilization of membrane proteins.…”