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DNA Cleavage by a Nine‐Membered Masked Enediyne, an Analogue of the Kedarcidin and C‐1027 Chromophores
Author(s) -
Takahashi Takashi,
Tanaka Hiroshi,
Yamada Haruo,
Matsumoto Takuyuki,
Sugiura Yukio
Publication year - 1996
Publication title -
angewandte chemie international edition in english
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 5.831
H-Index - 550
eISSN - 1521-3773
pISSN - 0570-0833
DOI - 10.1002/anie.199618351
Subject(s) - enediyne , cleavage (geology) , chromophore , dna , chemistry , stereochemistry , ring (chemistry) , photochemistry , biochemistry , biology , organic chemistry , fracture (geology) , paleontology
A phthalate group serves as the trigger for controlling the stability of the enediyne precursor 1 . β‐Elimination of this trigger generates the corresponding enediyne and the DNA‐cleaving biradical. The highly strained nine‐membered ring in 1 , an analogue of the kedarcidin chromophore, was constructed by a transannular [2,3] Wittig rearrangement. Incubation of supercoiled DNA with 1 (1 m M ) leads to double strand cleavage without the addition of a reducing agent, which is required for other DNA cleaving systems.