207117-28-0Relevant articles and documents
Mucin architecture behind the immune response: Design, evaluation and conformational analysis of an antitumor vaccine derived from an unnatural MUC1 fragment
Martínez-Sáez, Nuria,Supekar, Nitin T.,Wolfert, Margreet A.,Bermejo, Iris A.,Hurtado-Guerrero, Ramón,Asensio, Juan L.,Jiménez-Barbero, Jesús,Busto, Jesús H.,Avenoza, Alberto,Boons, Geert-Jan,Peregrina, Jesús M.,Corzana, Francisco
, p. 2294 - 2301 (2016)
A tripartite cancer vaccine candidate, containing a quaternary amino acid (α-methylserine) in the most immunogenic domain of MUC1, has been synthesized and examined for antigenic properties in transgenic mice. The vaccine which is glycosylated with GalNAc at the unnatural amino acid, was capable of eliciting potent antibody responses recognizing both glycosylated and unglycosylated tumour-associated MUC1 peptides and native MUC1 antigen present on cancer cells. The peptide backbone of the novel vaccine presents the bioactive conformation in solution and is more resistant to enzymatic degradation than the natural counter part. In spite of these features, the immune response elicited by the unnatural vaccine was not improved compared to a vaccine candidate containing natural threonine. These observations were rationalized by conformational studies, indicating that the presentation and dynamics of the sugar moiety displayed by the MUC1 derivative play a critical role in immune recognition. It is clear that engineered MUC1-based vaccines bearing unnatural amino acids have to be able to emulate the conformational properties of the glycosidic linkage between the GalNAc and the threonine residues. The results described here will be helpful to the rational design of efficacious cancer vaccines.
SELENOCYSTINE DERIVATIVES, ALPHA-METHYLSELENOCYSTEINE, ALPHA-METHYLSELENOCYSTEINE DERIVATIVES, AND METHODS OF MAKING AND USING SAME
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Paragraph 0086, (2016/08/29)
Provided are selenocysteine derivatives (e.g., deuterium and tritium analogs), α-methylselenocysteine, and α-methylselenocysteine derivatives. These compounds can be incorporated in more complex chemical structures (e.g., polymers, proteins, peptides, and
Synthesis of a new conformationally constrained glycoamino acid building block
Avenoza, Alberto,Peregrina, Jesús M.,San Martín, Emilio
, p. 6413 - 6416 (2007/10/03)
The synthesis of a suitably protected β-D-glucopyranosyl-(S)-α-methylserine derivative - a new conformationally constrained glycosylated quaternary amino acid analogue of β-D-glucopyranosyl-L-serine - is described. This compound can be used as an attractive building block for the synthesis of new, constrained glycopeptides.
