| Bergman cyclization of acyclic amino acid derived enediynes leads to the formation of 2,3-dihydrobenzo[f]isoindoles. | |
| | |
MedLine Citation:
|
PMID: 20718455 Owner: NLM Status: MEDLINE |
Abstract/OtherAbstract:
|
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 S(N)2 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. |
| | |
Authors:
|
Matija Gredicak; Ivana Matanović; Boris Zimmermann; Ivanka Jerić |
Related Documents
:
|
2675845 - Discriminator base of trna(asp) is involved in amino acid acceptor activity. 14652075 - Using a solid-phase ribozyme aminoacylation system to reprogram the genetic code. 7424225 - Synthesis of phospholipids in microstructures, prepared by the interaction of ammonium ... 12903125 - Aminoacylation of trna by antisense molecule. 1686905 - Lysophosphatidic acids induce contraction of rat isolated colon by two different mechan... 2700215 - Host-parasite relationships in candidosis. |
Publication Detail:
|
Type: Journal Article; Research Support, Non-U.S. Gov't |
Journal Detail:
|
Title: The Journal of organic chemistry Volume: 75 ISSN: 1520-6904 ISO Abbreviation: J. Org. Chem. Publication Date: 2010 Sep |
Date Detail:
|
Created Date: 2010-09-10 Completed Date: 2011-01-11 Revised Date: - |
Medline Journal Info:
|
Nlm Unique ID: 2985193R Medline TA: J Org Chem Country: United States |
Other Details:
|
Languages: eng Pagination: 6219-28 Citation Subset: IM |
Affiliation:
|
Division of Organic Chemistry and Biochemistry, Ruder Bosković Institute, Zagreb, 10000-HR Croatia. |
Export Citation:
|
APA/MLA Format Download EndNote Download BibTex |
| MeSH Terms | |
Descriptor/Qualifier:
|
Amino Acids
/
chemistry* Cyclization Enediynes / chemistry* Isoindoles / chemical synthesis*, chemistry Molecular Dynamics Simulation Molecular Structure Stereoisomerism |
| Chemical | |
Reg. No./Substance:
|
0/2,3-dihydrobenzo(f)isoindole; 0/Amino Acids; 0/Enediynes; 0/Isoindoles |
From MEDLINE®/PubMed®, a database of the U.S. National Library of Medicine
Previous Document: Undulations enhance the effect of helical structure on DNA interactions.
Next Document: Anion ZEKE-spectroscopy of the weakly bound iodine water complex.