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Cover Picture: Total Synthesis of 34‐Hydroxyasimicin and Its Photoactive Derivative for Affinity Labeling of the Mitochondrial Complex I (Chem. Eur. J. 9/2004)
Author(s) -
Han Hongna,
Sinha Mantosh K.,
D'Souza Lawrence J.,
Keinan Ehud,
Sinha Subhash C.
Publication year - 2004
Publication title -
chemistry – a european journal
Language(s) - English
Resource type - Reports
SCImago Journal Rank - 1.687
H-Index - 242
eISSN - 1521-3765
pISSN - 0947-6539
DOI - 10.1002/chem.200490027
Subject(s) - stereochemistry , chemistry , derivative (finance) , cytoplasm , oxidoreductase , biochemistry , enzyme , financial economics , economics
The cover picture shows representative plants of the Annonaceae plants (background), a family of tropical trees and shrubs that accommodates over 2300 species. More than 350 acetogenins have already been isolated from 37 species in this family, many of which have shown to be potent cytotoxic, antitumor, antimalarial, immunosuppressing, pesticidal, and antifeedant agents. It has been previously proposed that the cellular target of many Annonaceous acetogenins is the mitochondrial NADH–ubiquinone oxidoreductase (Complex I). The electron microscopic three‐dimensional reconstructions of Complex I (lower right corner) from N. crassa (wire frame) and the homologous E. coli complex (surface rendered) show that the two complexes have similar structures. The cytoplasmic domain for E. coli is colored in gold and the membrane domain in blue. The surfaces of the membrane are shown schematically in red (T. Friedrich et al., Biochim. Biophys. Acta 1998 , 1365 , 215). All acetogenins shown in the picture were previously synthesized by the Keinan–Sinha group. The asymmetric total synthesis of 34‐acyloxy‐34‐tritio‐asimicin (bottom) was achieved by means of a convergent synthetic strategy. This photoaffinity labeling agent is designed to identify the target protein subunit in Complex I. For more details see the article by E. Keinan, S. C. Sinha et al. on p. 2149 ff.