94164-89-3Relevant academic research and scientific papers
Straightforward, racemization-free synthesis of peptides with fairly to very bulky di- and trisubstituted glycines
Pinto, Filipa C.S.C.,Pereira-Lima, Sílvia M.M.A.,Maia, Hernani L.S.
scheme or table, p. 9165 - 9179 (2009/12/28)
Several fully protected tri- and pentapeptides containing a central symmetrical α,α-dialkyl glycine residue, with the alkyl group varying from methyl or ethyl to benzyl, were synthesized in good yields by a strategy based on the Ugi-Passerini reaction. Ea
An improved approach for the synthesis of α,α-dialkyl glycine derivatives by the Ugi-Passerini reaction
Costa, Susana P.G.,Maia, Hernani L.S.,Pereira-Lima, Silvia M.M.A.
, p. 1475 - 1479 (2007/10/03)
A general and simple strategy for routine peptide synthesis with α,α-dialkyl glycines taking advantage of the four-component Ugi-Passerini reaction is presented. The isonitrile required for the reaction can be relatively simple and its selection based on cost, as the group it generates is easily removed under acidic conditions; in addition, this removal is not visibly affected by the bulkiness of the α-alkyl groups. Being a good leaving group from the N-terminal amino group of the amino acid, 4-methoxybenzyl was the choice for the amine component of the reaction. The method is illustrated with the synthesis of a series of acyl derivatives of several α,α-dialkyl glycines. The preparation of the latter compounds is also reported.
