The search for new amphiphiles: synthesis of a modular, high-throughput library

Abstract

SummaryAmphiphilic compounds are used in a variety of applications due to their lyotropic liquid-crystalline phase formation, however only a limited number of compounds, in a potentially limitless field, are currently in use. A library of organic amphiphilic compounds was synthesised consisting of glucose, galactose, lactose, xylose and mannose head groups and double and triple-chain hydrophobic tails. A modular, high-throughput approach was developed, whereby head and tail components were conjugated using the copper-catalysed azide–alkyne cycloaddition (CuAAC) reaction. The tails were synthesised from two core alkyne-tethered intermediates, which were subsequently functionalised with hydrocarbon chains varying in length and degree of unsaturation and branching, while the five sugar head groups were selected with ranging substitution patterns and anomeric linkages. A library of 80 amphiphiles was subsequently produced, using a 24-vial array, with the majority formed in very good to excellent yields. A preliminary assessment of the liquid-crystalline phase behaviour is also presented.

β-Xylopyranosides: synthesis and applications

“…Glycosyl azides are valuable carbohydrate building-blocks as synthetic precursors of glycosylamines 124,127 and are widely used in "click chemistry" for the synthesis of N-glycosyl triazoles. [127][128][129][130] b-D-Xylopyranosyl azide can be obtained from 1,2,3,4-tetra-Oacetyl-b-D-xylopyranose in the presence of a Lewis acid (e.g., SnCl 4 , FeCl 3 , etc.) in CH 2 Cl 2 with trimethylsilyl azide (Fig.…”

Engineering specific chemical modification sites into a collagen‐like protein from Streptococcus pyogenes

“…The availability of maleimidyl reagents that allow active site precursors for “click” chemistry to be readily attached to the Cys‐modified bacterial collagens presents the greatest opportunity for production of a wide range of derivatives for functional evaluation. Whether either an alkyne or an azide is attached to the protein, large numbers (>100) of partner reagents are readily available for further reactions …”

Peptide-targeted dendrimeric prodrugs of 5-aminolevulinic acid: A novel approach towards enhanced accumulation of protoporphyrin IX for photodynamic therapy

“…The readily available amino triol derivative 1 employed by Battah et al [40] was chosen as the basis for the required ligatable ALA dendrons incorporating three ALA units. As shown in Scheme 2, selective N-acylation of 1 with pentynoic acid was achieved in 66% yield, using mild carboxyl activation via in situ mixed anhydride formation with EEDQ, as described by Feast [50]. The final ligatable ALA dendron 4, was then obtained in high yield by DMAP-catalysed esterification of the hydroxyl functions with Boc-ALA 3, using EDC as the coupling agent.…”