Even after more than 50 years since its discovery, the electrophilic potential of diazirines was never truly exploited. This longstanding limitation has been resolved. N-Monosubstituted diaziridines and hydrazones are obtained by nucleophilic additions. They release, under hydrolysis conditions, the corresponding monosubstituted hydrazines. The latter were converted to pyrazoles in high yields. The adamantanone can be recovered in 80-100% yields. This work demonstrates the potential of diazirines as electrophilic nitrogen sources with recoverable protecting groups.

Aminoacyl-tRNAs serve as amino acid donors in many reactions in addition to protein synthesis by the ribosome, including synthesis of the peptidoglycan network in the cell wall of bacterial pathogens. Synthesis of analogs of aminoacylated tRNAs is critical to further improve the mechanism of these reactions. Here we have described the synthesis of two non-isomerizable analogues of Ala-tRNA(Ala) containing an amide bond instead of the isomerizable ester that connects the amino acid with the terminal adenosine in the natural substrate. The non-isomerizable 2' and 3' regioisomers were not used as substrates by FemX(Wv), an alanyl-transferase essential for peptidoglycan synthesis, but inhibited this enzyme with IC50 of 5.8 and 5.5 μM, respectively.

N-Monosubstituted diaziridines release, under hydrolysis conditions, the corresponding monosubstituted hydrazines which are further converted into pyrazoles in high yields. The adamantanone can be recovered in 80-100% yield. This work demonstrates the potential of diazirines as electrophilic nitrogen sources with recoverable protecting groups. -(SCHNEIDER, Y.; PREVOST, J.; GOBIN, M.; LEGAULT*, C. Y.; Org. Lett. 16 (2014) 2, 596-599, http://dx.doi.org/10.1021/ol403495e ; Dep. Chem., Univ. Sherbrooke, Sherbrooke, Que. J1K 2R1, Can.; Eng.) -S. Adam 26-129

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