85995-50-2Relevant articles and documents
Simplified beta-glycosylation of peptides
Zhang, Yonglian,Knapp, Spencer
, p. 2891 - 2903 (2018/05/08)
A simple and effective activating system for S-phenyl thioglycosides, namely N-iodosuccinimide and catalytic copper(I) triflate, promotes beta-O-glycosylation at the serine and threonine hydroxyls of “mono-,” di-, and tripeptides. The same activator combination promotes carboxamide beta-N-glycosylation of asparagine-containing mono-, di, and tri-peptides, as well as a nucleoside carboxamide and a sulfonamide. An important feature of the copper(I) triflate method is that undesired amide O-glycosylation is largely circumvented. For both sets of biologically important acceptor sites (HO– and –CONH2), a beta-GlcNAc-equivalent donor is demonstrated to provide the linkages efficiently. Streamlined deprotection sequences have been developed based on global hydrogenolysis that lead smoothly to the parent glycopeptides. The core glycopeptide region for biological protein N-glycosylation, represented by N4-(β-N-acetyl-D-2-glucosaminyl)-Asp-Gly-Thr-OH, has been prepared in solution, purified, and characterized as the fully deprotected (mono)glycosylated tripeptide.
Synthesis and evaluation of lysophosphatidylserine analogues as inducers of mast cell degranulation. Potent activities of lysophosphatidylthreonine and its 2-deoxy derivative
Iwashita, Masazumi,Makide, Kumiko,Nonomura, Taro,Misumi, Yoshimasa,Otani, Yuko,Ishida, Mayuko,Taguchi, Ryo,Tsujimoto, Masafumi,Aoki, Junken,Arai, Hiroyuki,Ohwada, Tomohiko
experimental part, p. 5837 - 5863 (2010/03/24)
In response to various exogenous stimuli, mast cells (MCs) release a wide variety of inflammatory mediators stored in their cytoplasmic granules and this release initiates subsequent allergic reactions. Lysophosphatidylserine (lysoPS) has been known as an exogenous inducer to potentiate histamine release from MCs, though even at submicromolar concentrations. In this study, through SAR studies on lysoPS against MC degranulation, we identified lysoPT, a threonine-containing lysophospholipid and its 2-deoxy derivative as novel strong agonists. LysoPT and its 2-deoxy derivative induced histamine release from MCs both in vitro and in vivo at a concentration less than one-tenth that of lysoPS. Notably, lysoPT did not activate a recently proposed lysoPS receptor on MCs, GPR34, demonstrating the presence of another undefined receptor reactive to both lysoPS and lysoPT that is involved in MC degranulation. Thus, the present strong agonists, lysoPT and its 2-deoxy derivative, will be useful tools to understand the mechanisms of lysoPS-induced activation of degranulation of MCs. 2009 American Chemical Society.
Synthesis of δ-(L-α-aminoadipoyl)-L-cysteinyl-D-(O-methyl)-D- allothreonine a substrate for isopenicillin-N synthase and its O-Methyl-D- threonine epimer
Petursson, Sigthor,Baldwin, Jack E.
, p. 6001 - 6010 (2007/10/03)
The paper describes the synthesis of two epimeric tripeptides δ-(L-α- aminoadipoyl)-L-cysteinyl-D-(O-methyl)-D-threonine (13) and δ-(L-α- aminoadipoyl)-L-cysteinyl-D-(O-methyl)-D-allothreonine (14), modified substrates for the isopenicillin-N synthase enz
