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Cylindrocyclophane f

WebF: R1 = R2 = H • Cylindrocyclophane A was first isolated in 1990 by Moore et al. from the blue-green algae Cylindrospermum licheniforme Kutzing. • Cylindrocyclophane B-F were later isolated in 1992 again by Moore et al. • This class of compounds has been found to be biologically active showing moderate cytotoxicity against several tumor ... WebJun 26, 2024 · ... 31 Using a structure-guided strategy, we identified the cyl gene cluster, which produces cylindrocyclophanes A−F ( Figure 3). 2 Annotation of the gene cluster revealed no obvious candidate...

Cylindrocyclophane Biosynthesis Involves Functionalization …

Cylindrocyclophanes are a class of cyclophane, a group of aromatic hydrocarbons composed of two benzene rings attached in a unique structure. Cylindrocyclophanes were the first cyclophanes found in nature, isolated from a species of cyanobacteria, and have proven to be an interesting … See more Before the cylindrocyclophanes, the cyclophanes had all been produced synthetically. However, when a culture of the cyanobacteria Cylindrospermum lichenforme was being evaluated for antitumor activity, … See more Cylindrocyclophanes are all [7,7] paracyclophanes, differing only in the functional groups present on C-1, C-14, C-29, and C-33. There are currently 16 cylindrocyclophanes … See more Since the cylindrocyclophanes have such a unique structure and exciting biological possibilities due to their cytotoxicity, there have been numerous efforts to create them synthetically in the laboratory. One of the first attempts was the total synthesis of cylindrocyclophane … See more When cylindrocyclophane A was discovered, it was during an evaluation of the cyanobacteria Cylindrospermum lichenforme for antitumor activity. It was shown that … See more Webcylindrocyclophane A C36H56O6 CID 10348304 - structure, chemical names, physical and chemical properties, classification, patents, literature, biological ... shanon gruchot md https://ilkleydesign.com

Effects of Halide Ions on the Carbamidocyclophane Biosynthesis in

WebJun 26, 2024 · An authentic standard of cylindrocyclophane F was isolated from C. licheniforme ATCC 29412 as described previously 14. Luria-Bertani Lennox (LB) medium … WebJul 24, 2024 · (b) Cylindrocyclophane F is synthesized through head-to-tail dimerization of (S,R)-1 catalyzed by CylK. We are interested in the mechanism of CylK-catalyzed Friedel-Crafts alkylation, especially... WebCylindrocyclophane F was isolated using a procedure adapted from Moore and co-workers.2 Freeze-dried C. licheniforme ATCC 29412 (1.36 g) was ground using a mortar and pestle and the resulting paste was suspended in 7:3 ethanol/water (500 mL) and stirred overnight at 4 ºC. Insoluble cell debris was removed by centrifugation (4,000 rpm x 10 … shanon grey

A new strategy for aromatic ring alkylation in cylindrocyclophane ...

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Cylindrocyclophane f

Structures of cylindrocyphanes a-f - ScienceDirect

WebJul 10, 2013 · We have recently identified the enzymes involved in the biosynthesis of the cylindrocyclophanes, a structurally unique family of natural products, and found that this pathway employs a remarkable... WebThe cylindrocyclophanes are a family of macrocyclic natural products reported to exhibit antibacterial activity. Little is known about the structural basis of this activity due to the challenges associated with their synthesis or isolation.

Cylindrocyclophane f

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WebCylindrocyclophane F (25) was obtained with good yield (71%) via a one-pot sequential reaction including methylation of the side chains and demethylation of the methoxy groups. Concomitantly, the route to cylindrocyclophane A (16) was envisaged through oxidation of alcohol to ketone, enol triflate formation and cross coupling with a Grignard ... WebOct 18, 2024 · CylK is the key enzyme to catalyze the formation of the cylindrocyclophane scaffold through the Friedel-Crafts alkylation reactions with regioselectivity and stereospecificity. Further research...

WebJan 20, 2016 · Except for cylindrocyclophane A (25), non-carbamoylated or diacetylated [7.7]paracyclophanes (e.g., cylindrocyclophane A 1 (21) and D (27)) tended to be slightly less potent against MRSA, especially against strains N315 and Mu50 (MICs in the range 0.8‒12.9 µM) than the other derivatives, as it has been reported previously for MRSA … WebSep 11, 2024 · A short and efficient total synthesis of the C 2 -symmetric (−)-cylindrocyclophane F is presented, using a cross olefin metathesis dimerization strategy for construction of the [7,7]-paracyclophane macrocycle.

WebCylindrocyclophanes are a class of cyclophane, a group of aromatic hydrocarbons composed of two benzene rings attached in a unique structure. Cylindrocyclophanes were the first cyclophanes found in nature, isolated from a species of cyanobacteria, and have proven to be an interesting group of compounds to study due to their unusual molecular …

WebJul 10, 2013 · Carbamidocyclophane F (1) showed potent anti-Mycobacterium tuberculosis activity in the microplate Alamar blue assay and low-oxygen-recovery assay with MIC …

WebCylK 4 nostcyclophane and merocyclophane natural products. (b) Cylindrocyclophane F is synthesized through head-to-tail dimerization of (S,R)-1catalyzed by CylK. In this article, we report the crystal structures of CylK in its apo form … shanon harrisWebWe discovered that biosynthesis of cylindrocyclophane F requires the use of two enzymes with unprecedented mechanisms. The first novel enzyme, called CylC, selectively chlorinates an unfunctionalized fatty acid using what is likely a diiron metal cofactor to activate an inert C–H bond. shanon hendroffWebFeb 25, 2024 · CylK is the only enzyme known to catalyze aromatic ring alkylation with an alkyl halide electrophile, a reaction that mirrors a classical nonenzymatic reaction known … shanon hendroff in pragueWebJan 22, 2016 · As a result, three new cylindrocyclophane-related alkylresorcinols, cylindrofridins A-C (1-3), and known cylindrocyclophanes (4-6) were detected and isolated from Cylindrospermum stagnale PCC 7417. Structures of 1-3 were elucidated by a combination of 1D and 2D NMR experiments, HRMS, and ECD spectroscopy. … pom shellWebThe cylindrocyclophanes were isolated in the early 1990s from the cyanobacterium Cylindrospermum licheniforme Kützing and were the first naturally-occurring … pom sheetsWebThe structures of the ketones 1004 and 1006 are analogous to the p-cyclophane 992 in Scheme 7.4, and all react to give the hydrocarbons 1005 and 1007 in good yields (5).The … shanon g schwimmer md paWebMay 6, 2000 · Cylindrocyclophane Biosynthesis Involves Functionalization of an Unactivated Carbon Center. Journal of the American Chemical … pom shrink rate