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Pregled bibliografske jedinice broj: 478573

Bergman cyclization of acyclic amino acid-derived enediynes leads to the formation of 2, 3-dihydro-benzo[f]isoindoles


Gredičak, Matija; Matanović, Ivana; Zimmermann, Boris; Jerić, Ivanka
Bergman cyclization of acyclic amino acid-derived enediynes leads to the formation of 2, 3-dihydro-benzo[f]isoindoles // Journal of organic chemistry, 75 (2010), 6219-6228 doi:101021/jo101302n (međunarodna recenzija, članak, znanstveni)


Naslov
Bergman cyclization of acyclic amino acid-derived enediynes leads to the formation of 2, 3-dihydro-benzo[f]isoindoles

Autori
Gredičak, Matija ; Matanović, Ivana ; Zimmermann, Boris ; Jerić, Ivanka

Izvornik
Journal of organic chemistry (0022-3263) 75 (2010); 6219-6228

Vrsta, podvrsta i kategorija rada
Radovi u časopisima, članak, znanstveni

Ključne riječi
Bergman cyclization; enediynes; amino acids

Sažetak
Enediyne-peptide conjugates are recently recognized as useful tools in targeting various proteins, while mechanism underlying 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 external donor is followed by SN2 substitution leading to 2, 3-dihydro-benzo[f]isoindoles. 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.

Izvorni jezik
Engleski

Znanstvena područja
Kemija



POVEZANOST RADA


Projekt / tema
098-0352851-2921 - Kontrola atomske i molekulske dinamike oblikovanim elektromagnetskim poljima (Nađa Došlić, )
098-0982904-2927 - Makrociklički ligandi, strukturne promjene otopina i molekularne spektroskopije (Goran Baranović, )
098-0982933-2936 - Kemijske preobrazbe prirodnih spojeva (Lidija Varga-Defterdarović, )

Ustanove
Institut "Ruđer Bošković", Zagreb

Citiraj ovu publikaciju

Gredičak, Matija; Matanović, Ivana; Zimmermann, Boris; Jerić, Ivanka
Bergman cyclization of acyclic amino acid-derived enediynes leads to the formation of 2, 3-dihydro-benzo[f]isoindoles // Journal of organic chemistry, 75 (2010), 6219-6228 doi:101021/jo101302n (međunarodna recenzija, članak, znanstveni)
Gredičak, M., Matanović, I., Zimmermann, B. & Jerić, I. (2010) Bergman cyclization of acyclic amino acid-derived enediynes leads to the formation of 2, 3-dihydro-benzo[f]isoindoles. Journal of organic chemistry, 75, 6219-6228 doi:101021/jo101302n.
@article{article, year = {2010}, pages = {6219-6228}, DOI = {101021/jo101302n}, keywords = {Bergman cyclization, enediynes, amino acids}, journal = {Journal of organic chemistry}, doi = {101021/jo101302n}, volume = {75}, issn = {0022-3263}, title = {Bergman cyclization of acyclic amino acid-derived enediynes leads to the formation of 2, 3-dihydro-benzo[f]isoindoles}, keyword = {Bergman cyclization, enediynes, amino acids} }

Časopis indeksira:


  • Current Contents Connect (CCC)
  • Web of Science Core Collection (WoSCC)
    • Science Citation Index Expanded (SCI-EXP)
    • SCI-EXP, SSCI i/ili A&HCI
  • Scopus


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