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Structures of Five Components of the Actinomycin Z Complex from Streptomycesfradiae, Two of Which Contain 4-Chlorothreonine

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Institut für Organische Chemie, Georg-August-Universität Göttingen, D-37077 Göttingen, Germany, Laboratory of Bioorganic Chemistry, National Institute of Diabetes, and Digestive and Kidney Diseases, National Institutes of Health, Bethesda, Maryland 20892-0820, and Developmental Therapeutics Program, National Cancer Institute, National Institutes of Health, Bethesda, Maryland 20892-7448
Cite this: J. Nat. Prod. 2000, 63, 3, 352–356
Publication Date (Web):February 12, 2000
https://doi.org/10.1021/np990416u
Copyright © 2000 American Chemical Society and American Society of Pharmacognosy

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    Abstract

    Structure elucidation of five components of the actinomycin Z complex (Z1−Z5) isolated from Streptomycesfradiae is described. The components were separated by Si gel column chromatography and TLC/PLC and analyzed by ESIMS, FABMS, LC−MS of derivatized hydrolysates, and 2D NMR techniques. This permitted determination of the complete structures of actinomycins Z1−Z5. In Z3 and Z5, site 1 of the β-depsipeptide is occupied by the rare 4-chloro-l-threonine, an amino acid not previously found in an actinomycin. The structural variants of the actinomycin Z complex have the molecular architecture typical of other actinomycins but possess greater structural diversity resulting from the presence of several highly unusual amino acids. Actinomycins Z3 and Z5, but not Z1, were more potent than actinomycin D in cytotoxicity assays against three tumor cell lines.

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     Institut für Organische Chemie, Georg-August-Universität Göttingen.

     Laboratory of Bioorganic Chemistry, National Institute of Diabetes, and Digestive and Kidney Diseases, NIH.

    *

     To whom correspondence should be addressed. Tel.:  (301) 435-9156. Fax:  (301) 480-4817. E-mail:  [email protected].

    §

     Developmental Therapeutics Program, National Cancer Institute, NIH.

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    2D NMR connectivity diagrams (TOCSY and NOESY) for actinomycins Z1 and Z5 and linked-scan FABMS data (analogous to Table 5) for actinomycins Z1−Z4. This information is available on the World Wide Web at http://pubs.acs.org.

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