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| Thesis Name： |
Reaction microarrays and small-molecule printing. |
| Usage： |
chemistry |
| Keyword： |
Reaction microarrays ,small-molecule printing |
| Remarks： |
The development of reaction microarrays, a new technique for the parallelenantiomeric excess measurement of tens-of-thousands of samples, and extensions of this methodologyare presented in this thesis. Inspiration for this work came from a desire to blend thehigh-throughput experimentation of combinatorial catalysis with the high-throughput analysis of DNAmicroarrays. We sought to adapt the high-throughput analytical format of DNA microarray technologyto the measurement of the enantiomeric composition of solutions of small molecules that wereenvisioned to arise from catalytic, enantioselective reactions.; Amino acid derivatives were contactprinted via DNA microarrayers and covalently attached to derivatized glass microscope slides. Twopseudoenantiomeric fluorescent chiral probes, Cy3-(R)-proline and Cy5-(S)-proline, were observed toprovide enantiomeric discrimination of these immobilized amino acids under amide couplingconditions. Kinetic resolution in this amide coupling step provided a ratio of fluorophores at eachprinted spot that was proportional to the enantiomeric ratio of amino acid at that spot. Laserscanning of the glass slides yielded a fluorescence intensity ratio of fluorophores at each printedspot that was used to calculate the enantiomeric excess of the original sample solutions. Theapplicability of the reaction microarray method for high-throughput analysis was demonstrated byrapid identification of two >99% ee samples of proline out of 15,552 total samples.; A generalstrategy for the immobilization of organic small molecules to a glass surface was also developed.Substrates were printed onto sulfonyl azide-derivatized glass slides, which were then photolyzedusing a handheld 365 nm UV lamp. Arrayed substrates were found to be covalently attached to thesurface via a presumed reactive nitrene intermediate. Biologically relevant small molecules,including those not possessing reactive functional groups, were immobilized on a glass surface usingthis photolytic sulfonyl azide decomposition strategy. These arrays were used to detect the bindingof small molecules by proteins.
Author: Korbel, Gregory Alan.
Unit: Harvard University. |
| Original file： |
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