Solid-phase synthesis of Stat3 inhibitors incorpor...[Bioorg Med Chem Lett. 2007]

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1: Bioorg Med Chem Lett. 2007 Feb 1;17(3):654-6. Epub 2006 Nov 6. Links

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

Mandal PK, Heard PA, Ren Z, Chen X, McMurray JS.

The University of Texas, MD Anderson Cancer Center, Department of Experimental Therapeutics, 1515 Holcombe Boulevard, Houston, TX 77030, USA.

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.

PMID: 17113289 [PubMed - indexed for MEDLINE]

PMCID: PMC2676682

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Cited by 1 PubMed Central article

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

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