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