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Glycogen synthase kinase-3 (GSK-3) is associated with various key biological processes, including glucose regulation, apoptosis, protein synthesis, cell signaling, cellular transport, gene transcription, proliferation, and intracellular communication. Accordingly, GSK-3 has been implicated in a wide variety of diseases and specifically targeted for both therapeutic and imaging applications by a large number of academic laboratories and pharmaceutical companies. Here, we review the structure, function, expression levels, and ligand-binding properties of GSK-3 and its connection to various diseases. A selected list of highly potent GSK-3 inhibitors, with IC50 50

Nuceophilic substitution of a benzylic alcohol; 4-methoxybenzyl chloride
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A range of cleavage reagents for peptides synthesized on 2-chlorotrityl resin has been described. TFE/AcOH/DCM (1:1:3) has been developed by Barbs [62]. Cleavage is also rapidly attained with 0.5% TFA/DCM as well as with HFIP/DCM (1:4 or 3:7) [63].

The initial synthesis used 4-methoxybenzyl chloride ..

Wuts, P. G. M., Wilson, P. D. and Paduraru, M. P. 2007. -Methoxybenzyl Chloride. e-EROS Encyclopedia of Reagents for Organic Synthesis. .
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As mentioned above, the generation and disappearance of Fmoc based chromophors allows the monitoring of the synthesis. Furthermore, samples may be taken to determine the load of Fmoc peptide. The completion of the deprotection reaction may be checked by cleaving samples and analyzing the obtained peptide.

Better results will be obtained by repeating a coupling with fresh reagents (and changing coupling parameters if a low conversion was obtained) rather than by prolonging the reaction. Generally, coupling protocols may be changed in the course of a synthesis, especially when optimizing an SPPS.

for synthesis of 4-Hydroxy-3-methoxybenzyl alcohol

Power ultrasound efficiently facilitates the rapid preparation and reaction of 4-methoxybenzyl chloride (PMB-Cl) 1 in providing protected phenolic ether intermediates for organic synthesis. Using two-phase systems in both the ultrasound-promoted preparation and reactions of PMB-Cl, typical runs produce PMB-protected products …
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95. Vasdev N, Garcia A, Stableford WT, Young AB, Meyer JH, Houle S. . Synthesis and ex vivo evaluation of carbon-11 labelled N-(4-methoxybenzyl)-N'-(5-nitro-1,3-thiazol-2-yl)urea ([11C]AR-A014418): a radiolabelled glycogen synthase kinase-3beta specific inhibitor for PET studies. 2005;15:5270-3

There are often challenges in synthetic chemistry or radiochemistry to obtain the desired probe once the biochemical and physiological characteristics are optimized. Depending on the imaging modality, the synthetic chemistry requirements may vary considerably. For example, optical probes are challenged to maximize photon yield while minimizing photobleaching. PET probes are challenged by their shorter half-life and dependence on automation to reduce radiation exposure. For a PET imaging agent to succeed, a reliable and efficient method of synthesis that is translatable across radiochemistry facilities must be established. Furthermore, the synthesis method must be amenable to current Good Manufacturing Practice (cGMP) methods with a comprehensive quality assurance program if the probe is to be applied in human subjects.

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4-Methoxybenzyl Chloride 824-94-2 | TCI America

The other approach is to introduce backbone protecting groups which will prevent the formation of hydrogen bonds. Such protection is made by the introduction of the Hmb group on the αnitrogen [53]. It has been shown that the presence of a Hmb unit every 6-7 residues is sufficient to disrupt the peptide aggregation [54]. The Hmb protected amino acid is introduced under the form of N,O-bis-Fmoc-N-(2hydroxy-4-methoxybenzyl) derivative, the O-Fmoc protection being cleaved during the following piperidine treatment. At the end of the synthesis the Hmb group is cleaved in the final TFA cleavage.

4-Methoxybenzyl Chloride 824-94-2 | TCI Chemicals …

Gebhardt et al.[] showed application of emodin (82) and its ethylenediamine analog 83 as non-ATP competitive inhibitors of GSK-3 (Table ). Addition of the ethylenediamine group on the emodin nucleus increased potency of inhibition (IC50 0.56±0.02 µM, 83), reduced cytotoxicity and generated an insulin sensitizing effect mediated by increasing hepatocellular glycogen and fatty acid biosynthesis. Selectivity's of compounds 82 and 83 were evaluated against twelve protein kinases including eleven of human protein kinases. Compound 83 showed high selectivity towards GSK-3β but 82 failed to do so.

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