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Bergman Cyclization of Acyclic Amino Acid Derived Enediynes Leads to the Formation of 2,3-Dihydrobenzofisoindoles

Gredičak, Matija; Matanović, Ivana; Zimmermann, Boris; Jerić, Ivanka (2010) Bergman Cyclization of Acyclic Amino Acid Derived Enediynes Leads to the Formation of 2,3-Dihydrobenzofisoindoles. Journal of Organic Chemistry, 75 (18). pp. 6219-6228. ISSN 0022-3263

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Enediyne-peptide conjugates are recently recognized as useful tools in targeting various proteins, while the mechanism underlying the observed activity remains somewhat unclear. Addressing these issues, we have prepared acyclic amino acid derived enediynes and disclosed a novel thermally induced cyclization-elimination pathway. Initial formation of 1,4-benzene diradical and H-atom abstraction from an external donor is followed by SN2 substitution leading to 2,3-dihydrobenzo- [f]isoindoles. The proposed mechanism is supported by experimental and computational data. Additionally, we showed that amino acid side chains, although placed three bonds away from acetylene terminuses, have an appreciable influence on the reactivity of studied enediynes. These results demonstrate that amino acid or peptide parts of enediyne-peptide conjugates cannot be considered as recognition elements exclusively but may also participate in various reactions through amine functionality.

Item Type: Article
Additional Information: This document is the Accepted Manuscript version of a Published Work that appeared in final form in Journal of Organic Chemistry, copyright © American Chemical Society after peer review and technical editing by the publisher. To access the final edited and published work see
Uncontrolled Keywords: Bergman cyclization; enediynes; amino acids; benzoisoindoles
Subjects: NATURAL SCIENCES > Chemistry > Organic Chemistry
Divisions: Division of Organic Chemistry and Biochemistry
Division of Physical Chemistry
Project titleProject leaderProject codeProject type
Kemijske preobrazbe prirodnih spojeva[16092] Lidija Varga-Defterdarović098-0982933-2936MZOS
Makrociklički ligandi, strukturne promjene otopina i molekularne spektroskopije[2046] Goran Baranović098-0982904-2927MZOS
Kontrola atomske i molekulske dinamike oblikovanim elektromagnetskim poljima[158946] Nađa Došlić098-0352851-2921MZOS
Depositing User: Matija Gredičak
Date Deposited: 13 Nov 2013 15:19
DOI: 10.1021/jo101302n

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