Literature DB >> 17113289

Solid-phase synthesis of Stat3 inhibitors incorporating O-carbamoylserine and O-carbamoylthreonine as glutamine mimics.

Pijus K Mandal1, Patricia A Heard, Zhiyong Ren, Xiaomin Chen, John S McMurray.   

Abstract

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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Year:  2006        PMID： 17113289      PMCID： PMC2676682          DOI： 10.1016/j.bmcl.2006.10.099

Source DB:  PubMed          Journal:  Bioorg Med Chem Lett        ISSN： 0960-894X            Impact factor:   2.823


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