“…Di(10-decanal) disulfide ( 5 ) was synthesized from di(10,11-dihydroxyundecyl) disulfide ( 4 ) (step E in Figure ). The synthesis of ( 4 ) was carried out as in Yeager et al, except for step B, the synthesis of 1-bromo-10,11-isopropylidene-undecene ( 2 ). 1 Synthesis of di(10-decanal) disulfide 5 .…”
Chemistry is described for the fabrication of DNA arrays on gold surfaces. Alkanethiols modified with terminal aldehyde groups are used to prepare a self-assembled monolayer (SAM). The aldehyde groups of the monolayer may be reacted with amine-modified oligonucleotides or other amine-bearing biomolecules to form a Schiff base, which may then be reduced to a stable secondary amine by treatment with sodium cyanoborohydride. The surface modifications and reactions are characterized by polarization modulation Fourier transform infrared reflection absorption spectroscopy (PM-FTIRRAS), and the accessibility, binding specificity, and stability of the DNA-modified surfaces are demonstrated in hybridization experiments.
“…Di(10-decanal) disulfide ( 5 ) was synthesized from di(10,11-dihydroxyundecyl) disulfide ( 4 ) (step E in Figure ). The synthesis of ( 4 ) was carried out as in Yeager et al, except for step B, the synthesis of 1-bromo-10,11-isopropylidene-undecene ( 2 ). 1 Synthesis of di(10-decanal) disulfide 5 .…”
Chemistry is described for the fabrication of DNA arrays on gold surfaces. Alkanethiols modified with terminal aldehyde groups are used to prepare a self-assembled monolayer (SAM). The aldehyde groups of the monolayer may be reacted with amine-modified oligonucleotides or other amine-bearing biomolecules to form a Schiff base, which may then be reduced to a stable secondary amine by treatment with sodium cyanoborohydride. The surface modifications and reactions are characterized by polarization modulation Fourier transform infrared reflection absorption spectroscopy (PM-FTIRRAS), and the accessibility, binding specificity, and stability of the DNA-modified surfaces are demonstrated in hybridization experiments.
“…By refluxing 4 equiv of piperazine with ethylene sulfide 19 in benzene, compound 11 was formed which then slowly oxidized to afford disulfide 12 , isolated in 97% yield. Disulfides 10 and 12 (Scheme ) were used as starting materials for subsequent S N Ar reactions, as these are essentially protected thiols . It is well established 15 that both thiols and disulfides can adsorb onto Au surfaces using a S−Au linkage, leading to the formation of highly ordered SAMs that show identical character.…”
Several donor-sigma acceptor (D-sigma-A) molecules with thioalkyl side chains have been prepared by ruthenium-activated nucleophilic aromatic substition (S(N)Ar) reactions. Selective substitution of chloride from cyclopentadienyl(1,4-dichlorobenzene)ruthenium by using piperazine derivatives as nucleophiles is addressed. This selectivity, in combination with further manipulation of the complexes, allows the preparation of unsymmetrically functionalized tetraalkyl-p-phenylenediamine (TAPD) units which are difficult to synthesize by traditional organic S(N)Ar conditions. Phenanthroline-assisted decomplexation of the product arene-RuCp systems under UV irradiation is described.
A mild and efficient method for formation of methylene acetals from 1,2- and 1,3-diols using methoxymethylphenylsulfide, 1,3-dibromo-5,5-dimethylhydantoin (DBDMH), and dibutylhydroxytoluene (BHT) is described. The use of BHT in this process suppresses side reactions and enables high-yielding formation of methylene acetals of various diols, including carbohydrate-type substrates.
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