449205-69-0Relevant academic research and scientific papers
Novel conformationally restricted glycoamino acids from glyco-α-aminonitriles as potent turn mimics in peptide synthesis
Nguyen Van Nhien, Albert,Ducatel, Hélène,Len, Christophe,Postel, Denis
, p. 3805 - 3808 (2002)
Our previously described glycoaminocyanation procedure using Ti(OiPr)4 and TMSiCN has been applied to introduce amino acid and peptide moieties on a monosaccharide. Selective reduction using NaNH4-CoCl2 and Pd(C), respectively, is described. Restricted conformation of the new glycoamino acids favours intramolecular cyclisation to give the corresponding oxopiperazine 5a-b and 12a-b. The target acyclic compound I was obtained when the peptide derivative was displaced from the complex using KCN. Hydrolysis of the glycospirohydantoin 18 to give the glycoamino acid II is also described.
Novel glycine like amino acids from glyco-α-aminonitriles as building blocks for peptide synthesis
Ducatel, Helene,Van Nhien, Albert Nguyen,Postel, Denis
, p. 67 - 81 (2008/09/17)
Our interest in the glycoaminocyanation reaction led us to apply this methodology to introduce amino acids on a monosaccharide using the N-terminal position. The GAAs described in this paper are characterized by having the amino and carboxylic acid functionalities on a disubstituted position of the saccharide backbone leading to α,α-disubstituted glycines. These new sugar amino acids showed a restricted conformation involving a spontaneous intramolecular cyclization between the C- and N-terminal positions during hydrolysis or hydrogenolysis to give the corresponding oxopiperazine. Tripeptide mimics were obtained by the introduction of an additional amino acid using one-pot conditions starting from these cyclic by-products under basic media. We demonstrated that these pseudo tripeptides are good candidates for extension of the peptidic scaffold and cyclization.
