O-Carbamoylserine and O-carbamoylthreonine are glutamine analogues that were incorporated into a Stat3 inhibitory peptide to probe the requirements of Gln at the pY+3 position. Fmoc-Ser-NHBn and Fmoc-Thr-NHBn were converted to nitrophenyl carbonates and were attached to Rink resin via a side-chain carbamate linkage. After assembly of the peptide, acid treatment resulted in O-carbamoylserine and O-carbamoylthreonine-containing peptides. The order of affinity for Stat3 was Gln > Ser(CONH2) >> Thr(CONH2) suggesting a relatively tight binding pocket for the side chain of glutamine.
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| http://www.ncbi.nlm.nih.gov/pmc/articles/PMC2676682 | PMC |
| http://dx.doi.org/10.1016/j.bmcl.2006.10.099 | DOI Listing |
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