Über die Struktur des Chartreusins (Vorläufige Mitteilung)

Simonitsch, E.; Eisenhuth, W.; Stamm, O; Schmid, Hans

doi:10.1002/hlca.19600430107

Cited by 30 publications

(4 citation statements)

References 9 publications

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“…Tailoring enzymes are predicted to oxidatively open one polyphenolic ring and reclose it as a lactone [125], which is the first potential example of the formation of this functional group not formed from the ACP-bound acetate. Chartreusin [126,127] and its related structures [128] show antibiotic and chemotherapeutic activity. Its type-II-PKS-derived aglycone core, chartarin, is derived from a tetracenomycin-type decaketide through a series of redox reactions and decarboxylation that enables the rearrangement [129][130][131].…”

Section: Figurementioning

confidence: 99%

Expanding the Biosynthetic Toolbox: The Potential and Challenges of In Vitro Type II Polyketide Synthase Research

Rivers,

Lowell

2024

SynBio

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Type II polyketide synthase (PKS) systems are a rich source of structurally diverse polycyclic aromatic compounds with clinically relevant antibiotic and chemotherapeutic properties. The enzymes responsible for synthesizing the polyketide core, known collectively as the minimal cassette, hold potential for applications in synthetic biology. The minimal cassette provides polyketides of different chain lengths, which interact with other enzymes that are responsible for the varied cyclization patterns. Additionally, the type II PKS enzyme clusters offer a wide repertoire of tailoring enzymes for oxidations, glycosylations, cyclizations, and rearrangements. This review begins with the variety of chemical space accessible with type II PKS systems including the recently discovered highly reducing variants that produce polyalkenes instead of the archetypical polyketide motif. The main discussion analyzes the previous approaches with an emphasis on further research that is needed to characterize the minimal cassette enzymes in vitro. Finally, the potential type II PKS systems hold the potential to offer new tools in biocatalysis and synthetic biology, particularly in the production of novel antibiotics and biofuels.

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Section: Figurementioning

confidence: 99%

Expanding the Biosynthetic Toolbox: The Potential and Challenges of In Vitro Type II Polyketide Synthase Research

Rivers,

Lowell

2024

SynBio

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“…125 Chartreusin 86 was shown to exhibit excellent antitumor activity against murine P388, L1210 leukemia and B16 melanoma cell lines, however its rapid elimination through the bile and slow gastrointestinal absorption limits its clinical potential. 125 Chartreusin 86 was shown to exhibit excellent antitumor activity against murine P388, L1210 leukemia and B16 melanoma cell lines, however its rapid elimination through the bile and slow gastrointestinal absorption limits its clinical potential.…”

Section: Naphthopyranones With Extended Ring Systemsmentioning

confidence: 99%

“…Chartreusin 86 was rst isolated in 1953 from the culture broth of soil-derived Streptomyces chartreusis and shown to have antibiotic activity, 124 the complete structure being elucidated in 1960. 125 Chartreusin 86 was shown to exhibit excellent antitumor activity against murine P388, L1210 leukemia and B16 melanoma cell lines, however its rapid elimination through the bile and slow gastrointestinal absorption limits its clinical potential. 126 In the search for related compounds with greater therapeutic potential, an unidentied actinomycete strain J907-21 isolated from a soil sample of El Salvador was shown to produce elsamicins A 88 and B 89.…”

Section: Naphthopyranones With Extended Ring Systemsmentioning

confidence: 99%

Naphthopyranones – isolation, bioactivity, biosynthesis and synthesis

Donner

2015

Nat. Prod. Rep.

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The 1H-naphtho[2,3-c]pyran-1-one (naphthopyranone) moiety forms the structural framework of a group of secondary metabolites that have been isolated from a range of organisms including fungi, bacteria, lichen and plants. This review documents the known naturally occurring naphthopyranones - their isolation, biosynthesis and biological activity. A survey of methods reported for the synthesis of naphthopyranone natural products is presented.

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“…6 Azetidinone derivatives are also recognized as transcatheter arterial chemoembolization (TACE) inhibitors 7 and agents with new biological activities, such as anticancer, 8 anticoccidial, 9 cardiovascular, 10 antiviral, 11 mutagenic, 12 anticonvulsant and anti-inflammatory agents. 20 Coumarins substituted with different heterocycles at the position 4 have been shown to possess promising antibacterial activity. The coumarin skeleton is also present in novobiocin 18 and other recently discovered antibiotics, such as coumermycin 19 and chartreusin.…”

Section: Introductionmentioning

confidence: 99%

Synthesis of 2-azetidinones substituted coumarin derivative

Mashelkar

Jha

Mashelkar

2012

JSCS

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α-Naphthol is converted into 4-methylbenzo[h]chromen-2-one by reacting with ethyl acetoacetate in the presence of bismuth trichloride which is then oxidized to 2-oxo-2H-benzo[h]chromene-4-carbaldehyde and then condensed with aromatic primary amines to give Schiff bases (3a-3d). These Schiff bases are then reacted with acid chlorides in the presence of base in toluene to give 1, 3, 4-substituted 2-azetidinones

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Über die Struktur des Chartreusins (Vorläufige Mitteilung)

Cited by 30 publications

References 9 publications

Expanding the Biosynthetic Toolbox: The Potential and Challenges of In Vitro Type II Polyketide Synthase Research

Expanding the Biosynthetic Toolbox: The Potential and Challenges of In Vitro Type II Polyketide Synthase Research

Naphthopyranones – isolation, bioactivity, biosynthesis and synthesis

Synthesis of 2-azetidinones substituted coumarin derivative

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