The Removal of the <i>t</i>-BOC Group by Electrochemically Generated Acid and Use of an Addressable Electrode Array for Peptide Synthesis

Maurer, Karl; McShea, Andy; Strathmann, Michael; Dill, Kilian

doi:10.1021/cc0498175

Cited by 51 publications

(62 citation statements)

References 13 publications

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“…In context of more general combinatorial chemistry, chemically labile protecting groups are by far more varied and widely used than photolabile groups, as well as significantly cheaper in biopolymer synthesis. Considering that electrochemical protecting group removal has been demonstrated in biomolecule synthesis and surface-immobilization by electro-reduction (32), -oxidation (33), -catalysis (34,35), and -generation of acids and bases (17,18), PEC-gated reactions should be applicable to the in situ combinatorial synthesis of other biopolymers and small molecules.…”

Section: Discussionmentioning

confidence: 99%

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Photoelectrochemical synthesis of DNA microarrays

Chow

Emig

Jacobson

2009

Proc. Natl. Acad. Sci. U.S.A.

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Optical addressing of semiconductor electrodes represents a powerful technology that enables the independent and parallel control of a very large number of electrical phenomena at the solidelectrolyte interface. To date, it has been used in a wide range of applications including electrophoretic manipulation, biomolecule sensing, and stimulating networks of neurons. Here, we have adapted this approach for the parallel addressing of redox reactions, and report the construction of a DNA microarray synthesis platform based on semiconductor photoelectrochemistry (PEC). An amorphous silicon photoconductor is activated by an optical projection system to create virtual electrodes capable of electrochemically generating protons; these PEC-generated protons then cleave the acid-labile dimethoxytrityl protecting groups of DNA phosphoramidite synthesis reagents with the requisite spatial selectivity to generate DNA microarrays. Furthermore, a thin-film porous glass dramatically increases the amount of DNA synthesized per chip by over an order of magnitude versus uncoated glass. This platform demonstrates that PEC can be used toward combinatorial bio-polymer and small molecule synthesis.combinatorial chemistry ͉ genomics ͉ opto-electronics ͉ phosphoramidite ͉ solid-phase synthesis

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Section: Discussionmentioning

confidence: 99%

“…This selectivity has previously been achieved by a variety of methods, such as ink-jet printing (10,11), UV photocleavage (12)(13)(14), photo-generating acids (15,16), electrochemically generating acids (17,18), and electrophoretic delivery of reagent-embedded dielectric particles (19). The PEC platform reported here ( Fig.…”

mentioning

confidence: 99%

Photoelectrochemical synthesis of DNA microarrays

Chow

Emig

Jacobson

2009

Proc. Natl. Acad. Sci. U.S.A.

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“…Using the electrochemical arrays described above, we have recently reported the development of an electrochemical system using diphenylhydrazine for the removal of the t-BOC protecting group during peptide synthesis [14], [15] and on spatially contained, Pd-mediated transformations such as the Wacker oxidation, [16] Heck reaction [17], alcohol oxidation [18], and Coumarin formation [19].…”

Section: Resultsmentioning

confidence: 99%

Electrochemically Generated Acid and Its Containment to 100 Micron Reaction Areas for the Production of DNA Microarrays

et al. 2006

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An addressable electrode array was used for the production of acid at sufficient concentration to allow deprotection of the dimethoxytrityl (DMT) protecting group from an overlaying substrate bound to a porous reaction layer. Containment of the generated acid to an active electrode of 100 micron diameter was achieved by the presence of an organic base. This procedure was then used for the production of a DNA array, in which synthesis was directed by the electrochemical removal of the DMT group during synthesis. The product array was found to have a detection sensitivity to as low as 0.5 pM DNA in a complex background sample.

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“…A similar in concept is strategy employed by Maurer et al [178], who generated deprotecting acid (for removal of the Boc group in peptide synthesis) by application of an electric current on an array of electrodes analogously to Egeland and Southern [179], who developed this technique for DNA array synthesis. An acid was generated by applying þ 3 V onto an array of platinum electrodes in a solution of diphenylhydrazine.…”

Section: Synthesis Of Peptide Arraysmentioning

confidence: 99%

Combinatorial/Library Peptide Synthesis

Lebl

2011

Amino Acids, Peptides and Proteins in Organic Chemistry

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The Removal of the t-BOC Group by Electrochemically Generated Acid and Use of an Addressable Electrode Array for Peptide Synthesis

Cited by 51 publications

References 13 publications

Photoelectrochemical synthesis of DNA microarrays

Photoelectrochemical synthesis of DNA microarrays

Electrochemically Generated Acid and Its Containment to 100 Micron Reaction Areas for the Production of DNA Microarrays

Combinatorial/Library Peptide Synthesis

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