Category: 920519-33-1

Traceless β-mercaptan-assisted activation of valinyl benzimidazolinones in peptide ligations was written by Wang, Yinglu;Han, Lin;Yuan, Ning;Wang, Hanxuan;Li, Hongxing;Liu, Jinrong;Chen, Huan;Zhang, Qiang;Dong, Suwei. And the article was included in Chemical Science in 2018.Recommanded Product: Fmoc-asn(trt)-ser(psime,mepro)-oh This article mentions the following:

Peptidyl thioesters or their surrogates with C-terminal β-branched hydrophobic amino acid residues usually exhibit poor reactivities in ligation reactions. Thus, activation using exogenous additives is required to ensure an acceptable reaction efficiency. Herein, we report a traceless ligation at Val-Xaa sites under mild thiol additive-free reaction conditions, whereby the introduction of β-mercaptan on the C-terminal valine residue effectively activates the otherwise unreactive N-acyl-benzimidazolinone (Nbz), and enables the use of a one-pot ligation-desulfurization strategy to generate the desired peptide products. The orthogonality between β-thiovaline-Nbz and a conventional alkyl thioester, as well as the convenient access to the former from readily available penicillamine, also allowed expedited assembly of the peptidic hormone β-LPH and hPTH analogs, based on a kinetically controlled one-pot three-segment ligation and desulfurization strategy. In the experiment, the researchers used many compounds, for example, Fmoc-asn(trt)-ser(psime,mepro)-oh (cas: 920519-33-1Recommanded Product: Fmoc-asn(trt)-ser(psime,mepro)-oh).

Fmoc-asn(trt)-ser(psime,mepro)-oh (cas: 920519-33-1) belongs to oxazolidine derivatives. Oxazolidines are well known as key portions of bioactive molecules or precursors of chiral molecules, as well as established chiral auxiliaries. 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.Recommanded Product: Fmoc-asn(trt)-ser(psime,mepro)-oh

Referemce:
Oxazolidine – Wikipedia,
Oxazolidine | C3H7NO – PubChem

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