The Experts below are selected from a list of 261 Experts worldwide ranked by ideXlab platform
Rolf Breinbauer - One of the best experts on this subject based on the ideXlab platform.
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labeling and natural post translational modification of peptides and proteins via chemoselective pd catalyzed prenylation of cysteine
Journal of the American Chemical Society, 2019Co-Authors: Thomas Schlatzer, Julia Kriegesmann, Hilmar Schroder, Melanie Trobe, Christian Lembacherfadum, Simone Santner, Alexander V Kravchuk, Christian F W Becker, Rolf BreinbauerAbstract:The prenylation of peptides and proteins is an important post-translational modification observed in vivo. We report that the Pd-catalyzed Tsuji–Trost Allylation with a Pd/BIPHEPHOS catalyst system allows the Allylation of Cys-containing peptides and proteins with complete chemoselectivity and high n/i regioselectivity. In contrast to recently established methods, which use non-native connections, the Pd-catalyzed prenylation produces the natural n-prenylthioether bond. In addition, a variety of biophysical probes such as affinity handles and fluorescent tags can be introduced into Cys-containing peptides and proteins. Furthermore, peptides containing two cysteine residues can be stapled or cyclized using homobifunctional allylic carbonate reagents.
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Labeling and Natural Post-Translational Modification of Peptides and Proteins via Chemoselective Pd-Catalyzed Prenylation of Cysteine.
Journal of the American Chemical Society, 2019Co-Authors: Thomas Schlatzer, Julia Kriegesmann, Hilmar Schroder, Melanie Trobe, Simone Santner, Alexander V Kravchuk, Christian F W Becker, Christian Lembacher-fadum, Rolf BreinbauerAbstract:The prenylation of peptides and proteins is an important post-translational modification observed in vivo. We report that the Pd-catalyzed Tsuji–Trost Allylation with a Pd/BIPHEPHOS catalyst system...
Thomas Schlatzer - One of the best experts on this subject based on the ideXlab platform.
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labeling and natural post translational modification of peptides and proteins via chemoselective pd catalyzed prenylation of cysteine
Journal of the American Chemical Society, 2019Co-Authors: Thomas Schlatzer, Julia Kriegesmann, Hilmar Schroder, Melanie Trobe, Christian Lembacherfadum, Simone Santner, Alexander V Kravchuk, Christian F W Becker, Rolf BreinbauerAbstract:The prenylation of peptides and proteins is an important post-translational modification observed in vivo. We report that the Pd-catalyzed Tsuji–Trost Allylation with a Pd/BIPHEPHOS catalyst system allows the Allylation of Cys-containing peptides and proteins with complete chemoselectivity and high n/i regioselectivity. In contrast to recently established methods, which use non-native connections, the Pd-catalyzed prenylation produces the natural n-prenylthioether bond. In addition, a variety of biophysical probes such as affinity handles and fluorescent tags can be introduced into Cys-containing peptides and proteins. Furthermore, peptides containing two cysteine residues can be stapled or cyclized using homobifunctional allylic carbonate reagents.
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Labeling and Natural Post-Translational Modification of Peptides and Proteins via Chemoselective Pd-Catalyzed Prenylation of Cysteine.
Journal of the American Chemical Society, 2019Co-Authors: Thomas Schlatzer, Julia Kriegesmann, Hilmar Schroder, Melanie Trobe, Simone Santner, Alexander V Kravchuk, Christian F W Becker, Christian Lembacher-fadum, Rolf BreinbauerAbstract:The prenylation of peptides and proteins is an important post-translational modification observed in vivo. We report that the Pd-catalyzed Tsuji–Trost Allylation with a Pd/BIPHEPHOS catalyst system...
J. Stephen Clark - One of the best experts on this subject based on the ideXlab platform.
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Stereoselective Synthesis of Medium-Sized Cyclic Ethers by Sequential Ring-Closing Metathesis and Tsuji-Trost Allylation.
Organic letters, 2018Co-Authors: James Skardon-duncan, Michael Sparenberg, Alexandre Bayle, Sam Alexander, J. Stephen ClarkAbstract:Fully functionalized medium-sized cyclic ethers, of the type found in fused polyether natural products, have been prepared by sequential ring-closing diene metathesis, conversion of the resulting cyclic enone into an allylic enol carbonate, and Tsuji–Trost Allylation using a chiral palladium complex. Very high levels of diastereocontrol, favoring the diastereomer in which there is a cis relationship between the allyl group at C-2 of the medium-ring ether and the substituent at C-7/C-8, are obtained in cases where catalyst control and substrate control are matched.
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Synthesis of the A–D Ring System of the Gambieric Acids
Organic letters, 2015Co-Authors: J. Stephen Clark, Filippo Romiti, Bora Sieng, Laura C. Paterson, Alister Stewart, Subhabrata Chaudhury, Lynne H. ThomasAbstract:The A–D fragment of gambieric acids A and C has been synthesized using an asymmetric Tsuji–Trost Allylation reaction to couple the two key segments. The A ring fragment has been prepared by a short and highly efficient route involving diastereoselective Lewis acid mediated alkylation of an acetal. Iterative ring-closing metathesis reactions have been used to construct cyclic ethers and assemble the tricyclic B–D fragment.
Yanxing Jia - One of the best experts on this subject based on the ideXlab platform.
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Total Syntheses of Festuclavine, Pyroclavine, Costaclavine, epi-Costaclavine, Pibocin A, 9-Deacetoxyfumigaclavine C, Fumigaclavine G, and Dihydrosetoclavine
Organic letters, 2017Co-Authors: Haichao Liu, Xiwu Zhang, Dong Shan, Mallesham Pitchakuntla, Yanxing JiaAbstract:A new approach for the divergent total synthesis of eight ergot alkaloids is reported. The approach allows the first total syntheses of pyroclavine, pibocin A, 9-deacetoxyfumigaclavine C, and fumigaclavine G and also enables the efficient synthesis of festuclavine, costaclavine, epi-costaclavine, and dihydrosetoclavine. The main feature of the synthesis is the use of an unprecedented Pd-catalyzed intramolecular Larock indole annulation/Tsuji–Trost Allylation cascade to assemble the tetracyclic core in one step.
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Total Syntheses of Festuclavine, Pyroclavine, Costaclavine, epi-Costaclavine, Pibocin A, 9‑Deacetoxyfumigaclavine C, Fumigaclavine G, and Dihydrosetoclavine
2017Co-Authors: Haichao Liu, Xiwu Zhang, Dong Shan, Mallesham Pitchakuntla, Yanxing JiaAbstract:A new approach for the divergent total synthesis of eight ergot alkaloids is reported. The approach allows the first total syntheses of pyroclavine, pibocin A, 9-deacetoxyfumigaclavine C, and fumigaclavine G and also enables the efficient synthesis of festuclavine, costaclavine, epi-costaclavine, and dihydrosetoclavine. The main feature of the synthesis is the use of an unprecedented Pd-catalyzed intramolecular Larock indole annulation/Tsuji–Trost Allylation cascade to assemble the tetracyclic core in one step
Christian F W Becker - One of the best experts on this subject based on the ideXlab platform.
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labeling and natural post translational modification of peptides and proteins via chemoselective pd catalyzed prenylation of cysteine
Journal of the American Chemical Society, 2019Co-Authors: Thomas Schlatzer, Julia Kriegesmann, Hilmar Schroder, Melanie Trobe, Christian Lembacherfadum, Simone Santner, Alexander V Kravchuk, Christian F W Becker, Rolf BreinbauerAbstract:The prenylation of peptides and proteins is an important post-translational modification observed in vivo. We report that the Pd-catalyzed Tsuji–Trost Allylation with a Pd/BIPHEPHOS catalyst system allows the Allylation of Cys-containing peptides and proteins with complete chemoselectivity and high n/i regioselectivity. In contrast to recently established methods, which use non-native connections, the Pd-catalyzed prenylation produces the natural n-prenylthioether bond. In addition, a variety of biophysical probes such as affinity handles and fluorescent tags can be introduced into Cys-containing peptides and proteins. Furthermore, peptides containing two cysteine residues can be stapled or cyclized using homobifunctional allylic carbonate reagents.
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Labeling and Natural Post-Translational Modification of Peptides and Proteins via Chemoselective Pd-Catalyzed Prenylation of Cysteine.
Journal of the American Chemical Society, 2019Co-Authors: Thomas Schlatzer, Julia Kriegesmann, Hilmar Schroder, Melanie Trobe, Simone Santner, Alexander V Kravchuk, Christian F W Becker, Christian Lembacher-fadum, Rolf BreinbauerAbstract:The prenylation of peptides and proteins is an important post-translational modification observed in vivo. We report that the Pd-catalyzed Tsuji–Trost Allylation with a Pd/BIPHEPHOS catalyst system...
