1983
DOI: 10.1002/bip.360220133
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Stabilizing effects of 2‐methylalanine residues on β‐turns and α‐helices

Abstract: Synopsis13C-, 'H-nmr, CD, and x-ray crystallography revealed @-turns of type 111 for BOC-G~Y-LAla-Aib-OMe, Boc-L-Ala-Aib-L-Ala-OMe; the 3lo-helix for Boc-Aib-L-Ala-Aib-L-Ala-AibOMe; and antiparallel arranged a-helices for Boc-L-Ala-Aib-Ala-Aib-Ala-Glu(0Bzl)-AlaAib-Ala-Aib-Ala-OMe. An N-terminal rigid a-helical segment is found in the polypeptide antibiotics alamethicin, suzukacillin, and trichotoxin. The a-helix dipole is essential for their voltage-dependent pore formation in lipid bilayer membranes, which is… Show more

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Cited by 42 publications
(10 citation statements)
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“…As most of these residues occur in the N-terminus, this interpretation is in agreement with the data which suggests that the N-terminus of alamethicin is more stable than the C-terminus (Esposito et al, 1987;Yee and O'Neil, 1992;Franklin et al, 1994;Yee et al, 1995) and that Ala(Me) residues can give remarkable conformational stability to helical peptides (Augspurger et al, 1995). The presence of an N-acetyl group may add additional stability to the N-terminus of the helix (Chakrabartty et al, 1993;Jung et al, 1983).…”
Section: Temperature Dependence Of the Carbonyl Chemical Shiftssupporting
confidence: 88%
“…As most of these residues occur in the N-terminus, this interpretation is in agreement with the data which suggests that the N-terminus of alamethicin is more stable than the C-terminus (Esposito et al, 1987;Yee and O'Neil, 1992;Franklin et al, 1994;Yee et al, 1995) and that Ala(Me) residues can give remarkable conformational stability to helical peptides (Augspurger et al, 1995). The presence of an N-acetyl group may add additional stability to the N-terminus of the helix (Chakrabartty et al, 1993;Jung et al, 1983).…”
Section: Temperature Dependence Of the Carbonyl Chemical Shiftssupporting
confidence: 88%
“…The flip-flop gating mechanism turns out to be the best framework for an understanding of the molecular mechanisms which lead to voltage-dependent formation of this type of channels. A preliminary report on part of the data has previously been presented (Jung et al, 1983b).…”
Section: Discussionmentioning
confidence: 99%
“…For this purpose we used a hydrophobic model of the antibiotic alamethicin [23], the fifteen amino acid polypeptide Boc-(L-Ala-Aib-LAla-Aib-L-Ala)3-OMe (where Boc = t-butyloxycarbonyl, ALIa = alznine, Aib = aminoisobutyric acid and OMe = methoxy), called P15, which was shown to be largely present as a-types helices in lipophilic solutions [24] due to the high aminoisobutyric acid content of the peptide [25]. This polypeptide and several analogues with different number of repeat units have been found to form voltage-dependent ion-conducting channels in black lipid membranes [26].…”
Section: Introductionmentioning
confidence: 99%