UK-63,052 complex, new quinomycin antibiotics from Streptomyces braegensis subsp. japonicus; Taxonomy, fermentation, isolation, characterisation and antimicrobial activity.

Total asymmetric syntheses of (1S,2S)-norcoronamic acid, and of (1R,2R)- and (1S,2S)-coronamic acids from the diastereoselective cyclization of 2-(N-benzylideneamino)-4-chlorobutyronitriles

“…N-Methyl (lS,2S)-norcoronamic acid l b , isolated from streptomyces braegensis subsp. japotzicus, has been found to be a constituent of the cyclic peptide portion of the recently discovered DNA-intercalating antibiotics of the quinomycin family (13).…”

Relative and Absolute Configuration of Antitumor Agent SW-163D

“…SNA15896 produced SW-163C (3) and SW-163E (5) 7,8) whose structures were closely related with those of UK-63052 derivatives 10) having different substituents at the thioacetal portion. In addition to these compounds, this strain produced structurally similar SW-163 derivatives.…”

“…1). Similarly, SW-163F (6: R = isopropyl) and SW-163G (7: R = sec-butyl) were identical to UK-65662 and UK-63052, 10) respec-tively. These observations showed that Streptomyces sp.…”

“…Using the procedure described above for 9, ent-9 was obtained as a colorless oil (55%). ent-9: [] (À)-Benzyl (1R, 2S)-carboxy-2-methylcyclopropane-1-carboxylate (10). To a solution of 9 (2.00 g, 6.30 mmol) in t-BuOH (34.0 ml)-H 2 O (6.8 ml) was added dropwise 1 M aq.…”

Exploring the Biosynthesis of Natural Products and Their Inherent Suitability for the Rational Design of Desirable Compounds through Genetic Engineering

“…As judged by detailed X-ray, NMR structural, and other biophysical studies of these molecules, heteroaromatic planar chromophores, the invariant feature of quinomycin antibiotics, provide these compounds with the ability to bis-intercalate tightly into DNA. [52][53][54] In addition, a comparative study of echinomycin and SW-163D [55][56][57][58] found that the type of chromophore in the compounds influences their sequence selectivity. 59) However, the cyclic peptide backbone of these molecules, while providing a rigid framework that holds the chromophores in place for effective DNA intercalation, also plays an important role in determining the binding sequence specificity of these antibiotics, primarily by forming hydrogen bonds with the base moieties in the minor groove.…”