Large-scale synthesis and structural analysis of a synthetic glycopeptide dendrimer as an anti-cancer vaccine candidate was written by Ganneau, Christelle;Simenel, Catherine;Emptas, Emeline;Courtiol, Tiphanie;Coic, Yves-Marie;Artaud, Cecile;Deriaud, Edith;Bonhomme, Frederic;Delepierre, Muriel;Leclerc, Claude;Lo-Man, Richard;Bay, Sylvie. And the article was included in Organic & Biomolecular Chemistry in 2017.Electric Literature of C44H41N3O7 This article mentions the following:
Herein, we report a new process that enables the gram-scale production of a fully synthetic anti-cancer vaccine for human use. This therapeutic vaccine candidate, named MAG-Tn3, is a high-mol.-weight tetrameric glycopeptide encompassing carbohydrate tumor-associated Tn antigen clusters and peptidic CD4+ T-cell epitopes. The synthetic process involves (i) the stepwise solid-phase assembly of protected amino acids, including the high value-added Tn building blocks with only 1.5 equiv, (ii) a single isolated intermediate, and (iii) the simultaneous deprotection of 36 hindered protective groups. The resulting MAG-Tn3 was unambiguously characterized using a combination of techniques, including a structural anal. by NMR spectroscopy. The four peptidic chains are flexible in solution, with a more constrained but extended conformation at the Tn3 antigen motif. Finally, we demonstrate that, when injected into HLA-DR1-expressing transgenic mice, this vaccine induces Tn-specific antibodies that mediate the killing of human Tn-pos. tumor cells. These studies led to a clin. batch of the MAG-Tn3, currently investigated in breast cancer patients (phase I clin. trial). The current study demonstrates the feasibility of the multigram-scale synthesis of a highly pure complex glycopeptide, and it opens new avenues for the use of synthetic glycopeptides as drugs in humans. In the experiment, the researchers used many compounds, for example, Fmoc-asn(trt)-ser(psime,mepro)-oh (cas: 920519-33-1Electric Literature of C44H41N3O7).
Fmoc-asn(trt)-ser(psime,mepro)-oh (cas: 920519-33-1) belongs to oxazolidine derivatives.Oxazolidines are readily available also from propargyl amines. Oxazolidines are cyclic condensation products of β-amino alcohols and aldehydes or ketone, and they undergo a facile and complete hydrolysis in aqueous solution. Alterations in carbonyl moiety control the rate of formation of a given β-amino alcohol.Electric Literature of C44H41N3O7
Referemce:
Oxazolidine – Wikipedia,
Oxazolidine | C3H7NO – PubChem