Structure of an aromatization product of C-1027 chromophore

Minami, Yoshinori; Yoshida, Kenichi; Azuma, Ryotaro; Saeki, Mayuko; Otani, Toshio

doi:10.1016/s0040-4039(00)77643-x

Cited by 92 publications

(38 citation statements)

References 18 publications

Supporting

Mentioning

Contrasting

Order By: Relevance

“…C-1027 consists of a nonpeptidic chromophore and an apoprotein, CagA (also called C-1027AG [36]). The C-1027 chromophore is extremely unstable in the protein-free state, and its structure was initially deduced from an inactive but more stable degradation product (32) and was subsequently confirmed by spectroscopic analysis of the natural product (54) (Fig. 1).…”

mentioning

confidence: 98%

Genes for Production of the Enediyne Antitumor Antibiotic C-1027 in Streptomyces globisporus Are Clustered with the cagA Gene That Encodes the C-1027 Apoprotein

Liu

Shen

2000

Antimicrob Agents Chemother

108

View full text Add to dashboard Cite

C-1027, the most potent member of the enediyne antitumor antibiotic family, is produced by Streptomyces globisporus C-1027 and consists of an apoprotein (encoded by the cagA gene) and a nonpeptidic chromophore. The C-1027 chromophore could be viewed as being derived biosynthetically from a benzoxazolinate, a deoxyamino hexose, a ␤-amino acid, and an enediyne core. By adopting a strategy for cloning of the C-1027 biosynthesis gene cluster by mapping a putative dNDP-glucose 4,6-dehydratase (NGDH) gene to cagA, we have localized 75 kb of contiguous DNA from S. globisporus. DNA sequence analysis of two regions of the cloned gene cluster revealed two genes, sgcA and sgcB, that encode an NGDH enzyme and a transmembrane efflux protein, respectively, and confirmed that the cagA gene resides approximately 14 kb upstream of the sgcAB locus. The involvement of the cloned gene cluster in C-1027 biosynthesis was demonstrated by disrupting the sgcA gene to generate C-1027-nonproducing mutants and by complementing the sgcA mutants in vivo to restore C-1027 production. These results represent the first cloning of a gene cluster for enediyne antitumor antibiotic biosynthesis and provide a starting point for future genetic and biochemical investigations of C-1027 biosynthesis.

show abstract

mentioning

confidence: 98%

Genes for Production of the Enediyne Antitumor Antibiotic C-1027 in Streptomyces globisporus Are Clustered with the cagA Gene That Encodes the C-1027 Apoprotein

Liu

Shen

2000

Antimicrob Agents Chemother

108

View full text Add to dashboard Cite

show abstract

“…Indeed, a large number of natural and synthetic bioactive compounds contain a 2H-1,4-benzoxazine scaffold [240]. For instance, the enediyne antitumor antibiotic, C-1027 [241] consists of a 2-methylene-3,4-dihydro-3-oxo-2H-1,4-benzoxazine moiety in the chromophore subunit. Many derivatives of 2H-1,4-benzoxazine have been reported as plant resistance factors against insects and also microbial diseases [242], serotonin-3 (5-HT3) receptor antagonists [243][244][245], potassium channel modulators [246], etc.…”

Section: Scheme 48 Mw-assisted Ugi 4-component Reaction Leading To Pmentioning

confidence: 99%

Microwave-Assisted Synthesis of Bioactive Six-Membered Heterocycles and Their Fused Analogues

et al. 2016

View full text Add to dashboard Cite

This review describes the formation of six-membered heterocyclic compounds and their fused analogues under microwave activation using modern organic transformations including cyclocondensation, cycloaddition, multicomponents and other modular reactions. The review is divided according to the main heterocycle types in order of increasing complexity, starting with heterocyclic systems containing one, two and three heteroatoms and their fused analogues. Recent microwave applications are reviewed, with special focus on the chemistry of bioactive compounds. Selected examples from the 2006 to 2015 literature are discussed.

show abstract

“…In the recent years, about 40 compounds containing this chromophor have been obtained [61] . One of them is C-1027 chromophore IV (298c) [450][451] , a sequence-specific double-strand DNA cleavage agent, which is cytotoxic at very low concentration (1.5 x 10 -17 M).…”

Section: Biological Properties Of Nafisamycinmentioning

confidence: 99%

A new 16-membered tetraene macrolide JBIR-100 from a newly identified Streptomyces species

Ueda¹,

Hashimoto²,

Yamamura³

et al. 2011

J Antibiot

View full text Add to dashboard Cite

Structure of an aromatization product of C-1027 chromophore

Cited by 92 publications

References 18 publications

Genes for Production of the Enediyne Antitumor Antibiotic C-1027 in Streptomyces globisporus Are Clustered with the cagA Gene That Encodes the C-1027 Apoprotein

Genes for Production of the Enediyne Antitumor Antibiotic C-1027 in Streptomyces globisporus Are Clustered with the cagA Gene That Encodes the C-1027 Apoprotein

Microwave-Assisted Synthesis of Bioactive Six-Membered Heterocycles and Their Fused Analogues

A new 16-membered tetraene macrolide JBIR-100 from a newly identified Streptomyces species

Contact Info

Product

Resources

About