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  • 1980-1984  (3)
  • Chemistry  (2)
  • Emerimicin  (1)
  • Polypeptide antibiotic
  • 1
    Electronic Resource
    Electronic Resource
    Circular dichroism and conformational analysis of the membrane-modifying peptide -N-t-Boc-(Aib-L-Ala)5-Gly-Ala-Aib-Pro-Ala-Aib-Aib-Glu-(OBzl)-Gln-OMe with respect to alamethicin (1980)
    New York : Wiley-Blackwell
    Biopolymers 19 (1980), S. 203-214 
    Details
    ISSN: 0006-3525
    Keywords: Chemistry ; Polymer and Materials Science
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Notes: The conformational analysis of the CD spectrum is reported for the synthetic and membrane-modifying nonadecapeptide analog of alamethicin N-t-Boc-(Aib-L-Ala)5-Gly-Ala-Aib-Pro-Ala-Aib-Aib-Glu(OBzl)- Gln-OMe. The CD data are evaluated according to three different methods and are discussed with respect to those obtained from natural alamethicin and suitable models such as N-t-Boc-(Aib-L-Ala)7-OPOE, fragments of the synthetic nonadecapeptide, and the hexadecapeptide N-t-Boc-(Aib-L-Ala)5-Pro-Ala-Aib-Aib-Glu(OBzl)-Gln-OMe. The synthetic nonadecapeptide with the longer helical region exhibits membrane activities comparable to those of alamethicin, whereas the hexadecapeptide with the shorter helix is inactive.
    Additional Material: 4 Ill.
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1002/bip.1980.360190114
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    Paper (German National Licenses)
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  • 2
    Electronic Resource
    Electronic Resource
    Stabilizing effects of 2-methylalanine residues on β-turns and α-helices (1983)
    New York : Wiley-Blackwell
    Biopolymers 22 (1983), S. 241-246 
    Details
    ISSN: 0006-3525
    Keywords: Chemistry ; Polymer and Materials Science
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Notes: 13C-, 1H-nmr, CD, and x-ray crystallography revealed β-turns of type III for Boc-Gly-L-Ala-Aib-OMe, Boc-L-Ala-Aib-L-Ala-OMe; the 310-helix for Boc-Aib-L-Ala-Aib-L-Ala-Aib-OMe; and antiparallel arranged α-helices for Boc-L-Ala-Aib-Ala-Aib-Ala-Glu(OBzl)-Ala-Aib-Ala-Aib-Ala-OMe. An N-terminal rigid α-helical segment is found in the polypeptide antibiotics alamethicin, suzukacillin, and trichotoxin. The α-helix dipole is essential for their voltage-dependent pore formation in lipid bilayer membranes, which is explained by a flip-flop gating mechanism based on dipole-dipole interactions of parallel and antiparallel arranged α-helices within oligomeric structures.
    Additional Material: 4 Ill.
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1002/bip.360220133
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    Paper (German National Licenses)
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  • 3
    Electronic Resource
    Electronic Resource
    Chromatographic and mass spectrometric characterization of the structures of the polypeptide antibiotics samarosporin and stilbellin and identity with emerimicin (1983)
    Springer
    Chromatographia 17 (1983), S. 679-685 
    Details
    ISSN: 1612-1112
    Keywords: Samarosporin ; Stilbellin ; Emerimicin ; Peptide Antibiotics (peptaibols) ; Fast atom bombardment MS ; Column liquid chromatography
    Source: Springer Online Journal Archives 1860-2000
    Topics: Chemistry and Pharmacology
    Notes: Summary The structural identity of the polypeptide antibiotics, samarosporin I(II) and stilbellin I(II) with emerimicin IV(III) has been established by thin-layer chromatography, quantitative amino acid analysis by ion-exchange chromatography, gas-liquid chromatography of the N-pentafluoropropionyl amino acid n-propyl esters and N,O-bis-pentafluoropropionyl phenylalaninol with quartz capillaries coated with the chiral stationary phase N-propionyl-L-valine-tert-butylamide, and determination of the relative molecular masses and sequence-specific fragments by field desorption fast atom bombardment mass spectrometry. The separation of closely related sequence analogues of the above polypeptides could be achieved by reversed-phase high-performance liquid chromatography with spherical, fully porous octadecylsilyl bonded phases, and 86% aqueous methanol as eluent. The application of both chromatographic and mass spectrometric methods is demonstrated to be most valuable for the characterization of antibiotics with the unusual constituents α-aminoisobutyric acid, isovaline and phenylalaninol. The methology employed is regarded to be applicable to all polypeptide antibiotics of the peptaibol class.
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1007/BF02259320
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    Paper (German National Licenses)
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