929294-62-2Relevant articles and documents
Solid-phase synthesis of Stat3 inhibitors incorporating O-carbamoylserine and O-carbamoylthreonine as glutamine mimics
Mandal, Pijus K.,Heard, Patricia A.,Ren, Zhiyong,Chen, Xiaomin,McMurray, John S.
, p. 654 - 656 (2007)
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.