TY  - JOUR
A1  - Lamping, Matthias
A1  - Enck, Sebastian
A1  - Geyer, Armin
T1  - Inverse γ-Turn-Inspired Peptide: Synthesis and Analysis of Segetalin A Indole Hemiaminal
JF  - European Journal of Organic Chemistry
N2  - 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.
KW  - Peptides
KW  - Aldehydes
KW  - Cyclization
KW  - Macrocycles
KW  - Nitrogen heterocycles
Y1  - 2015
U6  - http://dx.doi.org/10.1002/ejoc.201501179
SN  - 1099-0690
VL  - 2015
IS  - 34
SP  - 7443
EP  - 7448
ER  -