129397-81-5Relevant articles and documents
Model Studies on Protease-Catalysed Peptide Synthesis Using 9-Fluorenylmethoxycarbonyl Protected Amino Acid Derivatives
Kuhl, Peter,Saeuberlich, Simone,Jakubke, Hans-Dieter
, p. 1015 - 1022 (1992)
Fmoc-Phe-OMe, Fmoc-Ala-OMe and Fmoc-Gly-OH were coupled with H-Leu-NH2 under catalytic action of chymotrypsin, papain and thermolysin, respectively.The influence of different reaction media and several reaction parameters, such as reactants and enzyme con
Imidazotetrazines as Weighable Diazomethane Surrogates for Esterifications and Cyclopropanations
Svec, Riley L.,Hergenrother, Paul J.
supporting information, p. 1857 - 1862 (2019/12/27)
Diazomethane is one of the most versatile reagents in organic synthesis, but its utility is limited by its hazardous nature. Although alternative methods exist to perform the unique chemistry of diazomethane, these suffer from diminished reactivity and/or correspondingly harsher conditions. Herein, we describe the repurposing of imidazotetrazines (such as temozolomide, TMZ, the standard of care for glioblastoma) for use as synthetic precursors of alkyl diazonium reagents. TMZ was employed to conduct esterifications and metal-catalyzed cyclopropanations, and results show that methyl ester formation from a wide variety of substrates is especially efficient and operationally simple. TMZ is a commercially available solid that is non-explosive and non-toxic, and should find broad utility as a replacement for diazomethane.
Aqueous MW eco-friendly protocol for amino group protection
Nardi,Cano, N. Herrera,Costanzo,Oliverio,Sindona,Procopio
, p. 18751 - 18760 (2015/06/15)
In this paper a new catalyst-free and on-water method for protection of amines and amino acids with di-tert-butyl dicarbonate, 9-fluorenylmethoxycarbonyl chloride, acetyl chloride and tosyl chloride is presented. The protection can be realized in a few minutes under microwave-assistance. The reaction proved to be chemoselective in presence of ambident nucleophiles and water solution of di-tert-butyl carboxylic acid or chloride acid are the only wastes produced.