Pragmatic studies on protein-resistant self-assembled monolayers
The present study describes new synthetic routes to oligo(ethylene glycol)-terminated alkanethiols (OEG-ATs), starting from α,ω- dibromoalkanes, which are reacted either with OEG or with trityl mercaptan in the first step. In addition to these ether conju
Hahn, Christoph D.,Tinazli, Ali,Hoelzl, Martin,Leitner, Christa,Frederix, Filip,Lackner, Bernd,Mueller, Norbert,Klampfl, Christian,Tampe, Robert,Gruber, Hermann J.
New syntheses for 11-(mercaptoundecyl)triethylene glycol and mercaptododecyltriethyleneoxy biotin amide
Novel syntheses for mercaptododecyltriethyleneoxy biotin amide and 11-(mercaptoundecyl)triethylene glycol are presented here. Such alkyl thiols are popular components in creating monolayers capable of specifically binding proteins. The development of a variety of functionalized alkyl thiol compounds has a great impact on biosensor substrate design. In our synthesis of mercaptododecyltriethyleneoxy biotin amide, we couple aminotriethyleneoxydodecane disulfide to the NHS-activated biotin; this technique is amenable to attaching a carboxylated molecule of interest in order to create the functionalized alkyl thiol of choice. The 11-(mercaptoundecyl) triethylene glycol synthesis presented here is an alternative method easily completed in three steps.
Canaria, Christie A.,Smith, Jeffrey O.,Yu,Fraser, Scott E.,Lansford, Rusty
p. 4813 - 4816
(2007/10/03)
Formation of self-assembled monolayers by chemisorption of derivatives of oligo(ethylene glycol) of structure HS(CH2)11(OCH2CH2)mOH on gold
This paper describes the preparation of oligo(ethylene glycol)-terminated alkanethiols having structure HS-(CH2)11(OCH2CH2)mOH (m = 3-7) and their use in the formation of self-assembled monolayers (SAMs) on gold. A combination of experimental evidence derived from X-ray photoelectron spectroscopy (XPS), measurement of contact angles, and ellipsometry implies substantial disorder in the oligo(ethylene glycol)-containing segment. The order in the -(CH2)11- group is not denned by the available evidence. The SAMs are moderately hydrophilic: θa(H2O) = 34-38°; θr(H2O) = 22-25°. A study of monolayers containing mixtures of HS(CH2)11CH3 and HS(CH2)11(OCH2CH2)6OH suggests that the oligo(ethylene glycol) moieties are effective at preventing underlying methylene groups from influencing wetting by water. A limited study demonstrates that these oligo(ethylene glycol)-containing SAMs resist the adsorption of protein from solution and suggests that SAMs will be a useful model system for studying the adsorption of proteins onto organic surfaces.
Pale-Grosdemange, Catherine,Simon, Ethan S.,Prime, Kevin L.,Whitesides, George M.
p. 12 - 20
(2007/10/02)
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