Two cyclopeptides, celogentin L (1) and its epimer lyciumin A (2) were firstly isolated from Celosia argentea L.. The planar structures of the two compounds were fully determined by spectroscopic data, including 1D-, 2D-NMR, and HR-ESI/MS. The absolute configurations of amino acid components were as …
Functional Group Transformation: The Castle Synthesis of Celogentin C. Mark Cushman of Purdue University found (J. Org. Chem. 2010, 75, 3507. ) that a benzylic methyl ether 1 could be converted to the aldehyde 2 by N-bromosuccinimide. Two equivalents of NBS gave the methyl ester. Ning Jiao of Peking University used (Org. Lett. 2010, 12, 2888. Celogentin C (1, Figure 1) is a bicyclic octapeptide isolated by Kobayashi from the seeds of Celosia argentea. 1 It is a member of a growing family of structurally similar bicyclic peptides including moroidin 2 and celogentins A–J 3 as well as the related monocyclic peptides celogentin K 4 and stephanotic acid. 5 Many of these natural products inhibit the polymerization of tubulin, 6 with 1 One of our aims in pursuing the total synthesis of celogentin C was to prepare sufficient quantities of the natural product to enable anticancer screening. Kobayashi and coworkers demonstrated its potency as an antimitotic agent, 4 but prior to our work, there were no reports of its efficacy in antiproliferative assays employing cancer cells. We were able to synthesize a batch of material that was large enough for screening against the 60-cell-line panel of the National Cancer Institute. Aug 03, 2009 · The bicyclic octapeptide celogentin C (1, Figure 1) was isolated by Kobayashi and co‐workers from the seeds of Celosia argentea. 1 Other structurally similar natural products include the bicyclic peptides moroidin, 2 celogentins A–H, 3 and celogentin J, 3 as well as the monocyclic peptides celogentin K 4 and stephanotic acid. 5 Some of these compounds inhibit tubulin polymerization, 6 with 1 ranking as the most potent antimitotic agent of this natural product family.
2019-5-25 · Three new bicyclic peptides, celogentins A (1), B (2), and C (3), have been isolated together with a known-related peptide, moroidin (4), from the seeds of Celosia argentea, and their structures including absolute stereochemistry were determined by using extensive NMR methods and chemical means. Celogentins A (1), B (2), and C (3) inhibited the polymerization of tubulin, and celogentin C (3
Síntesis de indoles en la química orgánica. 2018-12-12 · Celogentin C, han inspirado a muchos químicos orgánicos sintéticos. El interés en desarrollar nuevas metodologías hacia una síntesis eficiente de este núcleo ha sido tema de investigación por muchos años. En esta revisión se presentan algunos los métodos clásicos y modernos para la síntesis del heterociclo. A general strategy for synthesis of cyclophane-braced
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The unusual molecular architecture of Celogentin C includes a tryptophan residue with substitution at C-2 and C-6 of the indole side chain, a biaryl-type system characterized by the C-N bond between the indole and imidazole moieties, and a beta-substituted amino acid that results from the cross-link between the tryptophan and leucine side chains. Synthesis of bioactive and stabilized cyclic peptides by Here, we describe the development of a highly versatile peptide macrocyclization strategy through a palladium-catalyzed C(sp 3)–H activation and the synthesis of cyclic peptides featuring unique hydrocarbon linkages between the β-carbon of amino acids and the aromatic side chains of Phe and Trp. We demonstrate that such peptides exhibit Antimicrobial activity of simplified mimics of celogentin C 2018-3-6 · Antimicrobial activity of simplified mimics of celogentin C Varsha J. Thombare a, b, James A. Holden b, c, Sreetama Pal d, e, Eric C. Reynolds b, c, Amitabha Chattopadhyay e, f, Neil M. O'Brien-Simpson b, c, Craig A. Hutton a, b, * a School of Chemistry, The University of Melbourne, Victoria 3010, Australia b Bio21 Molecular Science and Biotechnology Institute, The University of Melbourne The bicyclic octapeptide celogentin C (1, Figure 1) was isolated by Kobayashi and co-workers from the seeds of Celosia argentea. Other structurally similar natural products include the bicyclic peptides moroidin,celogentins A–H,and celogentin J,as well as the monocyclic peptides celogentin Kand stephanotic acid. Dec 15, 2019 · Easy-to-read patient leaflet for Cogentin. Includes indications, proper use, special instructions, precautions, and possible side effects.