160948-81-2Relevant academic research and scientific papers
Comparison of backbone modification in protein β-sheets by α→γ residue replacement and α-residue methylation
Lengyel, George A.,Reinert, Zachary E.,Griffith, Brian D.,Horne, W. Seth
supporting information, p. 5375 - 5381 (2014/07/21)
The mimicry of protein tertiary structure by oligomers with unnatural backbones is a significant contemporary research challenge. Among common elements of secondary structure found in natural proteins, sheets have proven the most difficult to address. Here, we report the systematic comparison of different strategies for peptide backbone modification in β-sheets with the goal of identifying the best method for replacing a multi-stranded sheet in a protein tertiary fold. The most effective sheet modifications examined led to native-like tertiary folding behavior with a thermodynamic folded stability comparable to the prototype protein on which the modified backbones are based. This journal is the Partner Organisations 2014.
Structure-affinity relationships of glutamine mimics incorporated into phosphopeptides targeted to the SH2 domain of signal transducer and activator of transcription 3
Mandal, Pijus K.,Ren, Zhiyong,Chen, Xiaomin,Xiong, Chiyi,McMurray, John S.
experimental part, p. 6126 - 6141 (2010/03/24)
In cancer cells, signal transducer and activator of transcription 3 (Stat3) participates in aberrant growth, survival, angiogenesis, and invasion signals and is a validated target for anticancer drug design. We are targeting its SH2 domain to prevent docking to cytokine and growth factor receptors and subsequent signaling. One of the important elements of the recognition sequence, pTyr-Xxx-Xxx-Gln, is glutamine. We incorporated novel Gln mimics into a lead peptide, pCinn-Leu-Pro-Gln-NHBn, and found that a linear, unconstrained side chain and carboxamide are necessary for high affinity, and the benzamide can be eliminated. Replacement of Gln-NHBn with (R)-4-aminopentanamide or 2-aminoethylurea produced inhibitors with equal or greater potency than that of the lead, as judged by fluorescence polarization (IC50 values were 110 and 130 nM, respectively). When Pro was replaced with cis-3,4- methanoproline, the glutamine mimic, (4R,5S)-4-amino-5-benzyloxyhexanamide resulted in an IC50 of 69 nM, the highest affinity Stat3 inhibitor reported to date. 2009 American Chemical Society.
Solid-phase synthesis of peptide vinyl sulfones as potential inhibitors and activity-based probes of cysteine proteases
Wang, Gang,Mahesh, Uttamchandani,Chen, Grace Y. J.,Yao, Shao Q.
, p. 737 - 740 (2007/10/03)
(Matrix presented) Peptide vinyl sulfones were prepared from 2-chlorotrityl resin-bound phenolic amino vinyl sulfones in high yield and purity. This method enables the convenient synthesis of peptide vinyl sulfones having different amino acids at the Psu
Synthesis of Chiral N-Protected α-Amino Aldehydes by Reduction of N-Protected N-Carboxyanhydrides (UNCAs)
Fehrentz, Jean-Alain,Pothion, Catherine,Califano, Jean-Christophe,Loffet, Albert,Martinez, Jean
, p. 9031 - 9034 (2007/10/02)
A facile one step synthesis of a wide variety of N-protected (Boc, Z, Fmoc) α-amino aldehydes under mild conditions is described.Pure N-protected (Boc, Z, Fmoc) α-amino aldehydes were obtained in high yields by reduction of N-protected (Z, Boc, Fmoc)-N-ca
