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1H nuclear magnetic resonance determination of the membrane-bound conformation of senktide, a highly selective neurokinin B agonist (1993)

Bersch, Beate ; Koehl, Patrice ; Nakatani, Yoichi ; [et al.]

Springer

Journal of biomolecular NMR 3 (1993), S. 443-461

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ISSN: 1573-5001

Keywords: Transferred NOE ; Distance geometry ; Tachykinin ; Active conformation ; NK3 receptor

Source: Springer Online Journal Archives 1860-2000

Topics: Biology , Chemistry and Pharmacology

Notes: Summary Senktide is a highly specific and potent analog of neurokinin B, the natural ligand of the tachykinin receptor NK-3. The membrane-bound conformation of senktide, interacting with negatively charged membrane vesicles composed of perdeuterated phosphatidylcholine and phosphatidylglycerol (70:30), has been investigated using two-dimensional transferred nuclear Overhauser effect spectroscopy (TRNOESY). The occurrence of an N-methylated phenylalanine in the peptide's sequence induces a cis-trans-isomerisation of the corresponding peptide bond which is slow on the chemical-shift scale. NMR data indicate a much stronger membrane affinity of the trans isomer, allowing the determination of a highly resolved membrane-bound conformation using distance geometry and energy minimization. The membrane-bound backbone conformation of several residues is found to be close to a left-handed helix, certainly due to the presence of nonnatural residues (succinylated N-terminal, N-methyl-phenylalanine) as well as a glycine. The results are discussed in the context of a possible biological relevance of the membrane-bound conformation, in terms of the affinity and specificity of this neuropeptide.

Type of Medium: Electronic Resource

URL: http://dx.doi.org/10.1007/BF00176010

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Studies on the Topography of Biomembranes: Regioselective Photolabelling in Vesicles with the Tandem Use of Cholesterol and a Photoactivable Transmembrane Phospholipidic Probe (1996)

Nakatani, Yoichi ; Yamamoto, Masakuni ; Diyizou, Yvonne ; [et al.]

Weinheim : Wiley-Blackwell

Chemistry - A European Journal 2 (1996), S. 129-138

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ISSN: 0947-6539

Keywords: bilayers ; cholesterol ; membrane ; probes ; phospholipids ; photolabelling ; Chemistry ; General Chemistry

Source: Wiley InterScience Backfile Collection 1832-2000

Topics: Chemistry and Pharmacology

Notes: 2H NMR, DSC and UV studies of DMPC (1,2-dimyristoyl-sn-glycero-3-phosphocholine) vesicles have demonstrated the favourable physicochemical properties of the transmembrane phospholipid probes 1 a and 1 b for membrane topographical studies. In particular, in the presence of a physiological amount of cholesterol, only one transmembrane conformation is observed. The use of 1 a and cholesterol together for photolabelling experiments in DMPC vesicles led to a remarkable improvement in the regioselectivity of cross-linking between 1 a and DMPC, and between 1 a and cholesterol: the myristoyl chains functionalized at C11, C12 and C13 made up 95% of the total photolabelled myristates, and cholesterol was principally functionalized at the C25 position on the side-chain. This indicates the formation of a highly ordered bilayer structure and proves directly the orientation of cholesterol perpendicular to the membrane plane with its chain terminal buried in the middle of the bilayer.

Additional Material: 11 Ill.