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The cis-trans isomerization of N-methyl-α,β-dehydroamino acids.
Autorzy
Rok wydania
2012
Czasopismo
Numer woluminu
98
Strony
466-478
DOI
10.1002/bip.22082.
Kolekcja
Język
Angielski
Typ publikacji
Artykuł
Abstract
Dehydroamino acids with the methylated N-terminal peptide group occur in natural small cyclic peptides. The structural analysis was used to investigate the cis-trans isomerization of the N-terminal tertiary amide group of diamides: Ac-(Z)-Δ(Me)Abu-NHMe (1), Ac-(Z)-Δ(Me)Phe-NHMe (2), Ac-(E)-Δ(Me)Phe-NHMe (3), Ac-Δ(Me)Ala-NHMe (4), and Ac-(Me)Ala-NHMe (5). The compounds were analyzed in the solid state by an X-ray crystallography (1-3), and in the solution by FTIR (MeCN and CHCl(3) ) and NMR (DMSO-d6 and CDCl(3) ) methods (1-5). In the solid state, the studied compounds adopt the cis configuration of N-terminal amide. In solution, this configuration also prevails for the dehydroamino acids 1-4, in contrast to the saturated analog 5. The results indicate that N-methyldehydroamino acids present a promising tool to induce the cis configuration of the amide bond.
Słowa kluczowe
dehydroamino acids, dehydropeptide, N-methylation
Adres publiczny
http://dx.doi.org/10.1002/bip.22082.
Strona internetowa wydawcy
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