Kedarcidin, a new chromoprotein antitumor antibiotic: structure elucidation of kedarcidin chromophore

Leet, John E.; Schroeder, Daniel R.; Hofstead, Sandra J.; Golik, Jerzy; Colson, Kimberly L.; Huang, Stella; Klohr, Steven E.; Doyle, Terrence W.; Matson, James A.

doi:10.1021/ja00046a071

Cited by 144 publications

(47 citation statements)

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“…They found that cis-1,5-hexadiyn-3-ene underwent an exclusively thermal rearrangement to generate a 1,4-didehydrobenzene intermediate which could easily be trapped by external reagents to yield benzene derivatives (Scheme 1) [3]. However, Bergman's research did not receive much attention until the late 1980s when the enediyne-type core structures of many naturally occurring antibiotics, such as calicheamicin [4,5], dynemicin A [6], esperamicin A 1 [7,8] and kedarcidin chromophore [9] were reported. The enediyne "warheads" of these antibiotics are readily triggered in vivo to generate 1,4-phenylene diradicals, which further cause DNA cleavage or crosslinking.…”

Section: Introductionmentioning

confidence: 99%

Recent advances of the Bergman cyclization in polymer science

Chen

2015

Sci. China Chem.

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The Bergman cyclization has strongly impacted on a number of fields including pharmaceutics, synthetic chemistry, and material science. The diradical intermediates stemmed from enediynes can not only cause DNA cleavage under physiological conditions but also function as monomer or initiator participants in polymer science. The homo-polymerization of enediynes through the Bergman cyclization to fabricate conjugated polymers is a fascinating strategy due to the advantages of facial operation, high efficiency, tailored structure, and catalyst-free operation. Moreover, conjugated polymers generated through the Bergman cyclization show many remarkable properties, such as excellent thermal stability, good solubility, and processability, which enables these polymers to be further manufactured into carbon-rich materials. Recent times have seen extensive efforts devoted to the application of the Bergman cyclization in polymer science and materials chemistry. A variety of synthetic strategies have been developed to fabricate structurally unique materials via the Bergman cyclization, including the fabrication of rod-like polymers with polyester, dendrimers and chiral imide side chains, functionalization of carbon nanomaterials by surface-grafting conjugated polymers, formation of nanoparticles by intramolecular collapse of single polymer chains, and the construction of carbon nanomembranes with different morphologies. Future developments involving the Bergman cyclization in polymer science, probably by altering the reaction mechanism to precisely control the microstructure of polymeric products, are also proposed in this review article.

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Section: Introductionmentioning

confidence: 99%

Recent advances of the Bergman cyclization in polymer science

Chen

2015

Sci. China Chem.

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“…1) (9,10) and kedarcidin chromophore (8, Fig. 1) (11), representing structurally distinct classes of enediyne antibiotics, were subsequently reported. Neocarzinostatin chromophore (9, Fig.…”

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confidence: 98%

Chemistry and biology of natural and designed enediynes.

Nicolaou

Smith²,

Yue³

1993

Proc. Natl. Acad. Sci. U.S.A.

248

172

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“…1 Neocarzinostatin, C-1027, and kedarcidine are naturally occurring DNA cleaving molecules, having a saccharide unit and a labile 9-membered enediyne moiety that can generate a reactive diradical. [2][3][4] We have reported the syntheses of monosaccharide conjugated enediynes I-IV and investigated the sequence selective cleavage of DNA, (i.e. the positions, 5'-CGG, 5'-CAG, and 5'-CGC) ( Figure 1).…”

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confidence: 99%

Parallel Synthesis of Oligosaccharide Conjugated Enediynes onto Silyl-linked Solid-Support

Matsuda¹,

Doi²,

Tanaka³

et al. 2001

Synlett

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A solid-phase synthesis of enediyne molecules containing a sugar moiety is reported. Polymer-supported (2-mercaptoethyl)glycosides linked through a trialkylsilane linker were coupled to a bromoacetate on an enediyne by S-alkylation. After simple washing of the polymer, mild acid treatment, and evaporation, the desired oligosaccharide conjugated enediynes were isolated in pure form in parallel fashion.

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Kedarcidin, a new chromoprotein antitumor antibiotic: structure elucidation of kedarcidin chromophore

Cited by 144 publications

References 1 publication

Recent advances of the Bergman cyclization in polymer science

Recent advances of the Bergman cyclization in polymer science

Chemistry and biology of natural and designed enediynes.

Parallel Synthesis of Oligosaccharide Conjugated Enediynes onto Silyl-linked Solid-Support

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