Chemoselectivity and the Chan-Lam Coupling Reaction: Adding Amino Acids to Polymer-Coated Microelectrode Arrays

The Journal of Organic Chemistry
Matthew D Graaf, Kevin D Moeller

Abstract

The placement of a peptide onto a microelectrode array is frequently complicated by the presence of multiple nucleophiles in the peptide. In the work reported here, we have found that the Chan-Lam coupling reactions used to site-selectively place thiol, alcohol, and amine nucleophiles onto diblock-copolymer-coated surfaces are chemoselective for the placement of thiol and alcohol nucleophiles on the arrays. This means that cysteine- and serine-containing peptides can be placed onto an array without any need to protect the N terminus of the peptide. Furthermore, it was found that placement of thiol groups onto an array with the Chan-Lam reaction using optimized reaction times leads to complete coverage of the electrodes. The extent of this coverage can be controlled by varying the reaction time in a manner that allows for the construction of arrays with a gradient of peptide concentrations.

References

Jun 9, 2007·Chemphyschem : a European Journal of Chemical Physics and Physical Chemistry·Eugene W L Chan, Muhammad N Yousaf
Dec 22, 2007·Science·Mario BeyerFrank Breitling
Oct 1, 1999·Analytical Chemistry·M G SullivanM D Ward
Jul 22, 2011·Langmuir : the ACS Journal of Surfaces and Colloids·Jennifer BartelsKevin D Moeller
Feb 7, 2014·Langmuir : the ACS Journal of Surfaces and Colloids·Bichlien H NguyenKevin D Moeller
Jul 16, 2014·Physical Chemistry Chemical Physics : PCCP·Mauro TorselloAntonino Polimeno
Dec 24, 2014·Langmuir : the ACS Journal of Surfaces and Colloids·Matthew D Graaf, Kevin D Moeller
Jun 5, 2015·Langmuir : the ACS Journal of Surfaces and Colloids·Ariel L FurstJacqueline K Barton

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Citations

Aug 31, 2018·Molecular Diversity·Iqra MunirRaheel Ahmad
Apr 17, 2021·Journal of the American Chemical Society·Benjamin R WalkerChristo S Sevov
May 26, 2018·Chemical Reviews·Koichi MitsudoSeiji Suga
Jun 2, 2018·Journal of the American Chemical Society·Nai-Hua YehKevin D Moeller
Oct 8, 2021·The Journal of Organic Chemistry·Ruby Krueger, Kevin D Moeller

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