Autor:	Sebastian Enck, Armin Geyer, Matthias Lamping
Rok vydání:	2015
Předmět:	chemistry.chemical_classification Indole test Stereochemistry Organic Chemistry Imine Peptide Cyclic peptide chemistry.chemical_compound chemistry Aminal Peptide synthesis Hemiaminal Peptide bond Physical and Theoretical Chemistry
Zdroj:	European Journal of Organic Chemistry. 2015:7443-7448
ISSN:	1434-193X
DOI:	10.1002/ejoc.201501179
Popis:	Substitution of a peptide bond for an imine transforms the irreversible macrocyclization of peptides into a reversible process. The inherent cyclization tendency of a linear peptide is then analyzable through the equilibrium between the aldehyde and the imine by virtue of the higher reactivity of the corresponding linear peptide aldehyde. The tryptophan side chain of segetalin A aldehyde forms a 12-membered cyclic indole hemiaminal instead of the 18-membered macrocyclic imine expected. Herein, we analyzed this uncommon hemiaminal that shows that the biosynthesis of cyclic peptides is not necessarily based on linear precursor peptides with a high inherent macrolactamization tendency.
Databáze:	OpenAIRE
Externí odkaz:	https://explore.openaire.eu/search/publication?articleId=doi_________::b1f472bafb8e2013313d7ecacba7f6f8 https://doi.org/10.1002/ejoc.201501179 Zobrazit plný text záznamu Plný text ve formátu PDF Plný text ve formátu HTML
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