A New Antibiotic CJ-17,665 from Aspergillus ochraceus.

Sugie, Yutaka; Hirai, Hideo; Inagaki, Taisuke; Ishiguro, Masaru; Kim, Yoonjeong; Kojima, Yasuhiro; Sakakibara, Tatsuo; Sakemi, Shinichi; Sugiura, Ayumu; Suzuki, Yumiko; Brennan, Lori; Duignan, Joan; Huang, Liang H.; Sutcliffe, Joyce A.; Kojima, Nakao

doi:10.7164/antibiotics.54.911

Cited by 103 publications

(67 citation statements)

References 10 publications

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“…Strukturell eng verwandt mit Stephacidin A (1) ist Avrainvillamid [13] (CJ-17665, [14] 3), das aus der Fermentationsbrühe von zwei Aspergillus-Stämmen gewonnen wurde. Die Produzenten wurden unabhängig voneinander aus einer vor den Bahamas gesammelten Probe von Grünalgen (Avrainvillae sp., marines Habitat) und aus einer venezolanischen Bodenprobe (terrestrisches Habitat) gewonnen.…”

Section: Methodsunclassified

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Stephacidin B: eine neue Komplexitätsstufe prenylierter Indol‐Alkaloide aus Pilzen

Nussbaum

2003

Angewandte Chemie

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Section: Methodsunclassified

“…Stephacidin [5] und verwandte Alkaloide [14,15] aus Aspergillus ochraceus (relative Stereochemie). Abbildung 1.…”

Section: Introductionunclassified

Stephacidin B: eine neue Komplexitätsstufe prenylierter Indol‐Alkaloide aus Pilzen

Nussbaum

2003

Angewandte Chemie

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“…7) from Aspergillus ochraceus. 87,88) The N-oxide of aspergamide B (named CJ-17,665) has recently been independently isolated from the same fungus by Sugie et al 88) These metabolites, including VM55599 are the only natural members of the paraherquamide family that do not have a spiro-ring system but rather, a 2,3-disubstituted indole-derived system.…”

Section: The Paraherquamides Marcfortines and Related Alkaloidsmentioning

confidence: 99%

Total Synthesis and Biosynthesis of the Paraherquamides: An Intriguing Story of the Biological Diels–Alder Construction

Williams

2002

Chem. Pharm. Bull.

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The paraherquamides constitute an unusual family of prenylated indole alkaloids that are secondary metabolites produced by Penicillium sp. and Aspergillus sp. fungi. This review will cover both the biosynthesis as well as the chemical synthesis of this family of natural products. Particular emphasis will be placed on the provocative hypothesis that the core bicyclo[2.2.2]diazaoctan ring system, which is common to this entire family, is formed by a biological DielsAlder reaction.Despite its widespread use in synthetic organic chemistry, the Diels-Alder cycloaddition reaction does not occur frequently in nature. 1,2) There are just a few reports in the literature claiming the identification of an enzyme that catalyzes this most ubiquitous synthetic ring-forming reaction. [3][4][5][6] A possible explanation for this is that, enzymes generally catalyze reactions by stabilizing the structure and charge of the developing transition state. For most reactions subject to this stratagem of catalysis, both the starting substrate and the product differ significantly with respect to structure from the transition state; it is this fundamental difference that allows for turnover; i.e., both the product and the starting substrate must bind to the enzyme less tightly than the transition state structure. In the Diels-Alder reaction, the transition state is highly ordered and closely resembles the structure of the product (see Fig. 1, below). In other words, an enzyme that was designed to stabilize the transition state structure for this reaction would be expected to be inhibited by the product (via tight binding) and turnover (thus catalysis) would be precluded. It is from within the excitement of this fundamental question, that this review will hold as a guiding light.The only examples of protein-catalyzed Diels-Alder reactions are those of catalytic antibodies that have recently been shown to catalyze the intermolecular [4ϩ2] cycloaddition reaction.7-9) In these cases, the initial Diels-Alder adducts were high-energy substances that significantly change their structure or conformation after the initial cyclocondensation and were subsequently released from the antibody CDR (allowing for turnover). In addition, ribozymes have been reported to catalyze the Diels-Alder reaction and findings in this area have been reviewed. 10) The Penicillium sp. that produces the brevianamides/paraherquamides may be a rare, but vitally important example of the existence of DielsAlderases. It is further significant to note in the context of the catalytic antibody stratagem that, the brevianamide DielsAlder adducts (which are proposed to be the brevianamides themselves) are very rigid substances; therefore, a significant change in conformation or structure is either impossible or highly unlikely. Elucidation of the mechanism for turnover in the purported paraherquamide and brevianamide [4ϩ2] cycloaddition reaction should be an extremely interesting and significant finding.In order to do proper justice to the history of the biosynthetic Diels-Alder p...

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“…They attracted attention due to their biological properties such as alteration of cardiovascular and bloodclotting functions (Long et al 2001;Einholm et al 2003). They also have activities as anti-tumor, antiviral, antifungal, and antibacterial (Nicholson et al 2006;Houston et al 2004;Sugie et al 2001;Kozlovsky et al 2003;Song et al 2003;Imamura and Prasad 2003). Some of their chemical properties are very interesting for medicinal chemistry, such as resistance to proteolysis, mimicking of peptidic pharmacophoric groups, conformational rigidity and their donor-acceptor properties for hydrogen bonding with biological targets (Wang et al 2002;Martins and Carvalho 2007).…”

Section: Introductionmentioning

confidence: 97%

Rapid synthesis of new block copolyurethanes derived from l-leucine cyclodipeptide in reusable molten ammonium salts: novel and efficient green media for the synthesis of new hydrolysable and biodegradable copolyurethanes

Rafiemanzelat

Abdollahi

2011

Amino Acids

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This study concerns the synthesis of novel multi block polyurethane (PU) copolymers containing cyclodipeptide, taking the advantage of ionic liquids (ILs) under microwave irradiation. For this, L-leucine anhydride cyclodipeptide (LACP) was prepared and then a new class of poly(ether-urethane-urea)s (PEUUs) was synthesized in molten ammonium type ILs. ILs were used as reaction media and PUs were prepared via two-step polymerization method. In the first step, 4,4'-methylene-bis-(4-phenylisocyanate) (MDI) was reacted with LACP to produce isocyanate-terminated oligo(imide-urea) as hard segment (NCO-OIU). Chain extension of the aforementioned pre-polymer with polyethyleneglycol (PEG) of molecular weights of 1000 (PEG-1000) was the second step to furnish a series of new PEUUs. These multiblock copolymers are thermally stable, soluble in amide-type solvents, hydrolysable and biodegradable. PEUUs prepared in ILs under microwave irradiation showed more phase separation and crystallinity than PEUUs prepared under conventional method. The protocol presented here has the merits of environmentally benign, simple operation, convenient work-up, short reaction time and good yields without using volatile organic solvents, and catalysts. Ammonium type reaction media were air and water stable, and relatively cheap, which makes them suitable for application. The results demonstrate that they can be easily separated into water and reused without losing activity. Reusability of tetrabutylammonium bromide as reaction media makes the method a cost effective and environmentally benign method under microwave irradiation. Thus, we could prepare environmentally friendly polymers via environmentally benign method.

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A New Antibiotic CJ-17,665 from Aspergillus ochraceus.

Cited by 103 publications

References 10 publications

Stephacidin B: eine neue Komplexitätsstufe prenylierter Indol‐Alkaloide aus Pilzen

Stephacidin B: eine neue Komplexitätsstufe prenylierter Indol‐Alkaloide aus Pilzen

Total Synthesis and Biosynthesis of the Paraherquamides: An Intriguing Story of the Biological Diels–Alder Construction

Rapid synthesis of new block copolyurethanes derived from l-leucine cyclodipeptide in reusable molten ammonium salts: novel and efficient green media for the synthesis of new hydrolysable and biodegradable copolyurethanes

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A New Antibiotic CJ-17,665 from Aspergillus ochraceus.

Cited by 103 publications

References 10 publications

Stephacidin B: eine neue Komplexitätsstufe prenylierter Indol‐Alkaloide aus Pilzen

Stephacidin B: eine neue Komplexitätsstufe prenylierter Indol‐Alkaloide aus Pilzen

Total Synthesis and Biosynthesis of the Paraherquamides: An Intriguing Story of the Biological Diels&ndash;Alder Construction

Rapid synthesis of new block copolyurethanes derived from l-leucine cyclodipeptide in reusable molten ammonium salts: novel and efficient green media for the synthesis of new hydrolysable and biodegradable copolyurethanes

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Total Synthesis and Biosynthesis of the Paraherquamides: An Intriguing Story of the Biological Diels–Alder Construction