Synthesis of New Components for Tethered Bilayer Membranes and Preliminary Surface Characterization.

Abstract

Two analogues of the membrane-forming species PhCH2SS(C24H40O14)(C20H41) (1) have been prepared via short synthetic routes. The compounds readily form self-assembled monolayers on gold. PhCH2SS(C27H45O16)(C20H41)2 PhCH2SS(C29H48O17)(C20H41)3

Solution- and Solid-Phase Synthesis of Components for Tethered Bilayer Membranes

“…While we, 14a,15c, and others, 14e,, have synthesized these materials by conventional solution-phase techniques, solid-phase techniques have not been employed in the preparation of such compounds, despite the suitability of the methodology to this class of materials. Other groups have employed solid-phase techniques in the synthesis of structurally similar molecules though for different usesthe synthesis of hydrophilic linkers for bioconjugation studies, and the synthesis of amphiphilic glycopyranosides for formation of stable liposomes, being two recent examples.…”

“…The principal material of the inner leaflet of the t-BLM reported by our group is the compound 1 which consists of a polyether component (derived from two tetraethylene glycol units linked via a succinate bridge) attached to a phytanyl chain. As part of ongoing studies examining the effect of molecular changes on biosensor function, the length of the hydrophilic component has been shown to correlate with the conductivity of the t-BLM, with longer linkers leading to greater membrane conductivity presumably as a result of an increased capacity for ions 14a…”

Influence of Specific Intermolecular Interactions on the Self-Assembly and Phase Behavior of Oligo(Ethylene Glycol)-Terminated Alkanethiolates on Gold

“…[12][13][14] Similarly, OEG spacers are useful in the formation of the supported lipid membranes. [15][16][17][18] In this case, the OEG SAMs serve as a hydrogellike matrix, separating the lipid phase from the solid support and thereby maintaining a liquid-crystalline structure of the biomimetic membrane. Therefore, the OEG SAMs also can be utilized in the design of interfacial layers for biosensors, DNA chips, and other bioanalytical devises.…”

“…During the past decade, they have been used as model surfaces in studies of protein adsorption phenomena, , thus mimicking properties of poly(ethylene glycol), a well-known protein- and cell-inert material. , Different types of OEG-terminated SAMs on gold, silver , and silicon have been investigated, including those assembled from the synthesized compounds and those prepared by reactions in situ on surfaces . Further on, soluble and flexible OEG chains in SAMs have been employed as a spacer for tethering of various biospecific groups in studies of molecular recognition events on surfaces. − Similarly, OEG spacers are useful in the formation of the supported lipid membranes. − In this case, the OEG SAMs serve as a hydrogellike matrix, separating the lipid phase from the solid support and thereby maintaining a liquid-crystalline structure of the biomimetic membrane. Therefore, the OEG SAMs also can be utilized in the design of interfacial layers for biosensors, DNA chips, and other bioanalytical devises. − …”

Synthesis of a Nonavalent Mannoside Glycodendrimer Based on Pentaerythritol

“…Pentaerythritol mono- p -methoxybenzyl ether ( 16 ) was selected as a core to allow future extension by selective deprotection and further reaction of the exposed alcohol. Burns et al described a procedure of the synthesis of triol 16 , involving the reductive opening of the pentaerythritol mono- p -methoxybenzylidene acetal ( 13 ) with DIBAL in toluene at room temperature in good yield, but we were unable to repeat this procedure. Two alternatives were developed.…”