340732-79-8Relevant academic research and scientific papers
A Trifunctional Linker for Palmitoylation and Peptide and Protein Localization in Biological Membranes
Syga, ?ukasz,de Vries, Reinder H.,van Oosterhout, Hugo,Bartelds, Rianne,Boersma, Arnold J.,Roelfes, Gerard,Poolman, Bert
, p. 1320 - 1328 (2020)
Attachment of lipophilic groups is an important post-translational modification of proteins, which involves the coupling of one or more anchors such as fatty acids, isoprenoids, phospholipids, or glycosylphosphatidyl inositols. To study its impact on the membrane partitioning of hydrophobic peptides or proteins, we designed a tyrosine-based trifunctional linker. The linker allows the facile incorporation of two different functionalities at a cysteine residue in a single step. We determined the effect of the lipid modification on the membrane partitioning of the synthetic α-helical model peptide WALP with or without here and in all cases below; palmitoyl groups in giant unilamellar vesicles that contain a liquid-ordered (Lo) and liquid-disordered (Ld) phase. Introduction of two palmitoyl groups did not alter the localization of the membrane peptides, nor did the membrane thickness or lipid composition. In all cases, the peptide was retained in the Ld phase. These data demonstrate that the Lo domain in model membranes is highly unfavorable for a single membrane-spanning peptide.
Parallel β-sheet as a novel template for polymerization of diacetylene
Mori, Takeshi,Shimoyama, Kenji,Fukawa, Youichi,Minagawa, Keiji,Tanaka, Masami
, p. 116 - 117 (2005)
The peptide having diacetylene at its side group formed parallel β-sheet structure in crystalline solid, and solid-state polymerization of the diacetylene groups successfully occurred by UV irradiation or heating of the crystal. Copyright
A Ligand Selection Strategy Identifies Chemical Probes Targeting the Proteases of SARS-CoV-2
Pe?alver, Lilian,Schmid, Philipp,Szamosvári, Dávid,Schildknecht, Stefan,Globisch, Christoph,Sawade, Kevin,Peter, Christine,B?ttcher, Thomas
supporting information, p. 6799 - 6806 (2021/02/01)
Activity-based probes are valuable tools for chemical biology. However, finding probes that specifically target the active site of an enzyme remains a challenging task. Herein, we present a ligand selection strategy that allows to rapidly tailor electroph
Precursor-Directed Diversification of Cyclic Tetrapeptidic Pseudoxylallemycins
Guo, Huijuan,Schmidt, Alexander,Stephan, Philipp,Ragu?, Luka,Braga, Daniel,Kaiser, Marcel,Dahse, Hans-Martin,Weigel, Christiane,Lackner, Gerald,Beemelmanns, Christine
, p. 2307 - 2311 (2018/10/15)
Cyclic peptides containing non-proteinogenic amino acids often exhibit a broad bioactivity spectrum and many have entered clinical trials with good prospects for drug development. We recently reported the discovery of six cyclic tetrapeptides, pseudoxylallemycins A–F (1–6), from a termite-associated Pseudoxylaria sp. X802. These compounds contain a rare O-homoallenyl-l-tyrosine moiety and show promising antimicrobial activity against the Gram-negative pathogenic bacterium Pseudomonas aeruginosa. To perform more detailed structure–activity studies, we pursued a precursor-directed diversification strategy. Herein, we report the purification, identification, and testing of 21 new pseudoxylallemycin derivatives.
Total Synthesis of Microcystin-LF and Derivatives Thereof
Zemskov, Ivan,Altaner, Stefan,Dietrich, Daniel R.,Wittmann, Valentin
, p. 3680 - 3691 (2017/04/11)
Microcystins (MCs) are highly toxic natural products which are produced by cyanobacteria. They can be released to the water during harmful algal blooms and are a serious threat to animals and humans. Described is the total synthesis of the cyanotoxin micr
Palladium-Triggered Chemical Rescue of Intracellular Proteins via Genetically Encoded Allene-Caged Tyrosine
Wang, Jie,Zheng, Siqi,Liu, Yanjun,Zhang, Zhaoyue,Lin, Zhi,Li, Jiaofeng,Zhang, Gong,Wang, Xin,Li, Jie,Chen, Peng R.
, p. 15118 - 15121 (2016/12/06)
Chemical de-caging has emerged as an attractive strategy for gain-of-function study of proteins via small-molecule reagents. The previously reported chemical de-caging reactions have been largely centered on liberating the side chain of lysine on a given protein. Herein, we developed an allene-based caging moiety and the corresponding palladium de-caging reagents for chemical rescue of tyrosine (Tyr) activity on intracellular proteins. This bioorthogonal de-caging pair has been successfully applied to unmask enzymatic Tyr sites (e.g., Y671 on Taq polymerase and Y728 on Anthrax lethal factor) as well as the post-translational Tyr modification site (Y416 on Src kinase) in vitro and in living cells. Our strategy provides a general platform for chemical rescue of Tyr-dependent protein activity inside cells.
Oxidative α,ω-diyne coupling as an approach towards novel peptidic macrocycles
Verlinden,Geudens,Martins,Tourwé,Ballet,Verniest
supporting information, p. 9398 - 9404 (2015/09/15)
The Glaser-Hay diyne coupling proved to be an efficient cyclisation approach towards diyne containing peptidic macrocycles. A variety of tetrapeptide-based macrocyclic 1,3-diynes were obtained from O-propargylated serine or tyrosine residues using Cu(OAc)2·H2O and NiCl2 under an O2-atmosphere. The effect of the linear 1,3-diyne on peptide conformations was studied by NMR and compared with a macrocycle bearing a saturated linker.
Methods and compositions for labeling polypeptides
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, (2016/04/05)
Synthesis of many proteins is tightly controlled at the level of translation and plays an essential role in fundamental processes such as cell growth and proliferation, signaling, differentiation or death. Methods that allow imaging and identification of
MACROCYCLIC COMPOUNDS FOR INHIBITION OF INHIBITORS OF APOPTOSIS
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, (2014/05/24)
There are disclosed compounds that modulate the activity of inhibitors of apoptosis (IAPs), pharmaceutical compositions containing said compounds and methods of treating proliferative disorders and disorders of dysregulated apoptosis, such as cancer, utilizing the compounds of the invention.
MACROCYCLIC COMPOUNDS FOR INHIBITION OF INHIBITORS OF APOPTOSIS
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Page/Page column, (2014/05/20)
There are disclosed compounds that modulate the activity of inhibitors of apoptosis (IAPs), pharmaceutical compositions containing said compounds and methods of treating proliferative disorders and disorders of dysregulated apoptosis, such as cancer, util
