On Intrahelical Hydrogen Bonding and Stability of β-Helices: The behavior of someD ,L -alternating oligoleucines with anN-methylated residue
| Autor: | Emma Fenude-Schoch, Gian Paolo Lorenzi, Daniel Urs Römer, Heinz Rüegger |
|---|---|
| Rok vydání: | 1993 |
| Předmět: |
Chemistry
Stereochemistry Hydrogen bond Organic Chemistry Liquid phase Nuclear Overhauser effect Nuclear magnetic resonance spectroscopy Biochemistry Catalysis Relative stability Inorganic Chemistry Residue (chemistry) chemistry.chemical_compound β structure Drug Discovery Peptide synthesis Physical and Theoretical Chemistry |
| Zdroj: | Helvetica Chimica Acta. 76:451-458 |
| ISSN: | 0018-019X |
| DOI: | 10.1002/hlca.19930760129 |
| Popis: | An N methylated residue at the n – 3 position of the chain was used to reduce the maximum number of H-bonds realizable y some D,L-alternating oligopeptides in β4.4-, 5.6- and 5.6-helices and thus increase for the oligopeptides, the relative stability of larger β-helices. With D, L-alternating oligoleucines of the series Boc-Leun-OMe, however, this approach did not produce the helices expected. Although 7.2-helices with only one free NH per strand would theoretically be possible, the N-methylated oligoleucines formed instead flawed β4.4-helices having three free NH's in CHCl3 as well as in other solvents of low polarity. These observations confirm that the stability of β-helices does not depend only on the number of intra-or interstrand H-bonds, and corroborate the idea that β-helices with large cavities are inherently unstable. |
| Databáze: | OpenAIRE |
| Externí odkaz: |
|
Plný text