445396-26-9Relevant academic research and scientific papers
Synthesis of N-alkyl-Cα,α-dimethylglycine derivatives
Monteiro, Luis S.,Pereira-Lima, Silvia M.M.A.,Pereira, Sofia,Machado, Joao N.
, p. 170 - 180 (2014/10/15)
The application of trialkyloxonium tetrafluoroborates for N-alkylation of the nonnatural amino acid Cα, α-dimethylglycine is described. Several methyl esters of dimethylglycine protected with different amine protecting groups were subject to N-
Synthesis and use of 2H-azirin-3-amines as dipeptide synthons
Breitenmoser, Roland A.,Heimgartner, Heinz
, p. 885 - 912 (2007/10/03)
The synthesis of the new 2H-azirin-3-amines ('3-amino-2H-azirines') 11, 20, 28, and 33 as dipeptide synthons is described. The reactions of the starting amides with Lawesson reagent gave the corresponding thioamides, and consecutive treatment with COCl2, 1,4-diazabicyclo[2.2.2]octane (DABCO), and NaN3 led to the desired products. It is shown that these 2H-azirin-3-amines can conveniently be used as building blocks of the dipeptides Aib-(Me)Axx (Axx=alanine, valine), Aib-Homoproline, and Iva-Pro in the synthesis of several model peptides. However, some limitations apply for the synthesis of such 2H-azirin-3-amines. The starting material for the azirine synthesis, the corresponding thioamides, cannot generally be synthesized, and the 2H-azirin-3-amines could not be obtained in all cases from the thioamides prepared.
