- Late-Stage Macrocyclization of Bioactive Peptides with Internal Oxazole Motifs via Palladium-Catalyzed C-H Olefination
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Oxazole is an important pharmacophore and exists in the backbone of many bioactive peptide natural products and peptidomimetics. Efficient methods for the synthesis and direct functionalization of complex oxazole-containing peptides are in high demand. Herein, we report the late-stage site-selective functionalization of oxazole-containing peptides via palladium-catalyzed δ-C(sp2)-H olefination of phenylalanine, tryptophan, and tyrosine residues. This strategy utilizes oxazole motifs as internal directing groups and provides access to oxazole-containing peptide macrocycles with bioactivities.
- Liu, Shu,Cai, Chuangxu,Bai, Zengbing,Sheng, Wangjian,Tan, Jiantao,Wang, Huan
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Read Online
- Solid-Phase-Based Total Synthesis and Stereochemical Assignment of the Cryptic Natural Product Aurantizolicin
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The total synthesis and stereochemical assignment of the polyazole cyclopeptide aurantizolicin was achieved by connecting the solution synthesis of building blocks with solid-phase peptide synthesis. Macrothiolactonization and an aza-Wittig reaction provi
- Oberheide, Ansgar,Pflanze, Sebastian,Stallforth, Pierre,Arndt, Hans-Dieter
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supporting information
p. 729 - 732
(2019/01/21)
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- NOVEL FERROPORTIN INHIBITORS
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The invention relates to novel ferroportin inhibitors of the general formula (I) pharmaceutical compositions comprising them and the use thereof as medicaments, in particular for the prophylaxis and/or treatment of diseases caused by a lack of hepcidin or iron metabolism disorders, such as particularly iron overload states such as in particular thalassemia and hemochromatosis.
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Page/Page column 137; 138; 187; 263
(2017/05/10)
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- Total synthesis of Microcin B17 via a fragment condensation approach
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The total synthesis of the 43 amino acid antibacterial peptide Microcin B17 (MccB17) is described. The natural product was synthesized via a convergent approach from a heterocycle-derived peptide and peptide thioester fragments prepared via Fmoc-strategy solid phase peptide synthesis (SPPS). Final assembly was achieved in an efficient manner using two Ag(I)-assisted peptide ligation reactions to afford MccB17 in excellent overall yield.
- Thompson, Robert E.,Jolliffe, Katrina A.,Payne, Richard J.
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supporting information; experimental part
p. 680 - 683
(2011/05/03)
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- Method for preparing largazole analogs and uses thereof
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Analogs of largazole are described herein. Methods of treating cancer and blood disorders using largazole and largazole analogs and pharmaceutical compositions comprising the same are additionally described herein. Methods for preparing largazole analogs are likewise described.
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Page/Page column 37
(2010/03/02)
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- Synthesis and histone deacetylase inhibitory activity of largazole analogs: Alteration of the zinc-binding domain and macrocyclic scaffold
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Fourteen analogs of the marine natural product largazole have been prepared and assayed against histone deacetylases (HDACs) 1, 2, 3, and 6. Olefin cross-metathesis was used to efficiently access six variants of the side-chain zinc-binding domain, while adaptation of our previously reported modular synthesis allowed probing of the macrocyclic cap group.
- Bowers, Albert A.,West, Nathan,Newkirk, Tenaya L.,Troutman-Youngman, Annie E.,Schreiber, Stuart L.,Wiest, Olaf,Bradner, James E.,Williams, Robert M.
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supporting information; experimental part
p. 1301 - 1304
(2009/09/06)
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- Novel polyoxazole-based cyclopeptides from Streptomyces sp. Total synthesis of the cyclopeptide YM-216391 and synthetic studies towards telomestatin
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A convergent, complementary, synthetic approach to the contiguously linked tris-oxazole units 10, 11 and 12 in telomestatin (1) and YM-216391 (2) is described. The route involves coupling reactions between oxazole 4-carboxylic acids, viz16a, 16c, 16d and
- Deeley, Jon,Bertram, Anna,Pattenden, Gerald
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supporting information; experimental part
p. 1994 - 2010
(2009/01/31)
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- Oxazole and thiazole combinatorial libraries
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This invention provides a novel method for synthesizing an ensemble of peptides that allows for the generation of an unlimited number of antibiotic compounds. More specifically, the method comprises utilizes synthetic heterocyclic amino acids containing thaizole and/or oxazole as building blocks in a solid phase combinatorial synthesis to yield natural and unnatural antibiotic compounds.
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Page/Page column 10; Sheet 2
(2008/06/13)
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- Synthese natuerlich vorkommender, konformativ eingeschraenkter Oxazol- und Thiazol-haltiger Di- und Tripeptidmimetika
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Keywords: Aminosaeuren; Heterocyclen; Oxidationen; Peptidmimetica; Synthesemethoden
- Videnov, Georgi,Kaiser, Dietmar,Kempter, Christoph,Jung, Guenther
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p. 1604 - 1607
(2007/10/03)
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