Nalazite se na CroRIS probnoj okolini. Ovdje evidentirani podaci neće biti pohranjeni u Informacijskom sustavu znanosti RH. Ako je ovo greška, CroRIS produkcijskoj okolini moguće je pristupi putem poveznice www.croris.hr
izvor podataka: crosbi

Bergman cyclization of acyclic amino acid-derived enediynes leads to the formation of 2, 3-dihydro-benzo[f]isoindoles (CROSBI ID 165300)

Prilog u časopisu | izvorni znanstveni rad | međunarodna recenzija

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

Podaci o odgovornosti

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

engleski

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

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.

Bergman cyclization; enediynes; amino acids

nije evidentirano

nije evidentirano

nije evidentirano

nije evidentirano

nije evidentirano

nije evidentirano

Podaci o izdanju

75

2010.

6219-6228

objavljeno

0022-3263

101021/jo101302n

Povezanost rada

Kemija

Poveznice
Indeksiranost