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A photocaged, cyclopropene-containing analog of the amino acid neurotransmitter glutamate.

ABSTRACT: Substituted cyclopropenes serve as compact biorthogonal appendages that enable analysis of biomolecules in complex systems. Neurotransmitters, a chemically diverse group of biomolecules that control neuron excitation and inhibition, are not among the systems that have been studied using biorthogonal chemistry. Here we describe the synthesis of cyclopropene-containing analogs of the excitatory amino acid neurotransmitter glutamate starting from a Garner's aldehyde-derived alkyne. The deprotected cyclopropene glutamate was stable in solution but decomposed upon concentration. Appending a light-cleavable group improved the stability of the cyclopropene while simultaneously caging the neurotransmitter. This strategy has the potential to permit deployment of cyclopropene-modified glutamate as a bioorthogonal probe of the neurotransmitter glutamate in vivo with spatiotemporal precision.

SUBMITTER: Kumar P

PROVIDER: S-EPMC6150495 | biostudies-literature | 2016 Dec

REPOSITORIES: biostudies-literature

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A photocaged, cyclopropene-containing analog of the amino acid neurotransmitter glutamate.

Kumar Pratik P Shukhman David D Laughlin Scott T ST

Tetrahedron letters 20161111 51

Substituted cyclopropenes serve as compact biorthogonal appendages that enable analysis of biomolecules in complex systems. Neurotransmitters, a chemically diverse group of biomolecules that control neuron excitation and inhibition, are not among the systems that have been studied using biorthogonal chemistry. Here we describe the synthesis of cyclopropene-containing analogs of the excitatory amino acid neurotransmitter glutamate starting from a Garner's aldehyde-derived alkyne. The deprotected ...[more]

PMID: 30245532

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A photocaged, cyclopropene-containing analog of the amino acid neurotransmitter glutamate.

Publications

A photocaged, cyclopropene-containing analog of the amino acid neurotransmitter glutamate.

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