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Literature DB >> 26151942

Bioorthogonal labelling of living bacteria using unnatural amino acids containing nitrones and a nitrone derivative of vancomycin.

Douglas A MacKenzie¹, Allison R Sherratt, Mariya Chigrinova, Arnold J Kell, John Paul Pezacki.

Abstract

Unnatural D-amino acids bearing endocyclic nitrones were developed for live-cell labelling of the bacterial peptidoglycan layer. Metabolic incorporation of D-Lys and D-Ala derivatives bearing different endocyclic nitrones was observed in E. coli, L. innocua, and L. lactis. The incorporated nitrones of these bacteria then rapidly underwent strain-promoted alkyne-nitrone cycloaddition (SPANC) reactions affording chemically modified bacteria.

Entities: Chemical Species

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Year: 2015 PMID： 26151942 DOI： 10.1039/c5cc04901f

Source DB: PubMed Journal: Chem Commun (Camb) ISSN： 1359-7345 Impact factor: 6.222

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Cited

5 in total

1. Membrane-specific spin trap, 5-dodecylcarbamoyl-5-N-dodecylacetamide-1-pyroline-N-oxide (diC₁₂PO): theoretical, bioorthogonal fluorescence imaging and EPR studies.

Authors: Colwyn A Headley; Claire N Hoffman; Juliana M Freisen; Yongbin Han; Joseph M Macklin; Jay L Zweier; Antal Rockenbauer; Jeff Kuret; Frederick A Villamena
Journal: Org Biomol Chem Date: 2019-07-22 Impact factor: 3.876

Bioorthogonal labelling of living bacteria using unnatural amino acids containing nitrones and a nitrone derivative of vancomycin.

1. Membrane-specific spin trap, 5-dodecylcarbamoyl-5-N-dodecylacetamide-1-pyroline-N-oxide (diC₁₂PO): theoretical, bioorthogonal fluorescence imaging and EPR studies.

Review 2. Small Molecule Sensors Targeting the Bacterial Cell Wall.

3. D-Amino Acid Probes for Penicillin Binding Protein-based Bacterial Surface Labeling.

4. Predicting reactivity for bioorthogonal cycloadditions involving nitrones.

Review 5. Shedding light on biology of bacterial cells.

Bioorthogonal labelling of living bacteria using unnatural amino acids containing nitrones and a nitrone derivative of vancomycin.

1. Membrane-specific spin trap, 5-dodecylcarbamoyl-5-N-dodecylacetamide-1-pyroline-N-oxide (diC12PO): theoretical, bioorthogonal fluorescence imaging and EPR studies.

Review 2. Small Molecule Sensors Targeting the Bacterial Cell Wall.

3. D-Amino Acid Probes for Penicillin Binding Protein-based Bacterial Surface Labeling.

4. Predicting reactivity for bioorthogonal cycloadditions involving nitrones.

Review 5. Shedding light on biology of bacterial cells.

1. Membrane-specific spin trap, 5-dodecylcarbamoyl-5-N-dodecylacetamide-1-pyroline-N-oxide (diC₁₂PO): theoretical, bioorthogonal fluorescence imaging and EPR studies.