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  • 1
    Electronic Resource
    Electronic Resource
    Synthesis and physicochemical characterization of the lanthionine analog of somatostatin[1–14] (1994)
    Springer
    International journal of peptide research and therapeutics 1 (1994), S. 81-87 
    Details
    ISSN: 1573-3904
    Keywords: SRIF ; Somatostatin ; Lanthionine ; Kaiser-oxime resin ; Peptide cyclization ; PCOR ; Solid-phase peptide synthesis ; Fmoc cleavage with DBU
    Source: Springer Online Journal Archives 1860-2000
    Topics: Chemistry and Pharmacology
    Notes: Summary The synthesis of the lanthionine analog of somatostatin[1–14] on a Kaiser-oxime resin is described. The 12-residue peptide segment [3–14] was assembled and cyclized on the resin by using the method of peptide cyclization on an oxime resin (PCOR); the product was obtained with good yield (41%) and purity (94%). The Fmoc protecting group on the N-terminus was cleaved with DBU, followed by a 2+12 segment condensation in solution. The chromatographic (HPLC, CZE) and spectral (UV, NMR) properties of the lanthionine and the natural somatostatins have been studied and compared. Preliminary biological tests show that the lanthionine and the natural somatostatins exhibit similar binding affinities to somatostatin receptor SSTR2.
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1007/BF00126277
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  • 2
    Electronic Resource
    Electronic Resource
    Absolute configuration for peptidomimetic residues in bioactive peptides (1991)
    New York, NY [u.a.] : Wiley-Blackwell
    Chirality 3 (1991), S. 268-276 
    Details
    ISSN: 0899-0042
    Keywords: absolute configuration ; peptidomimetics ; retro-inverso modifications ; 2-aminocyclopentanecarboxylic acid ; nuclear magnetic resonance (NMR) ; nuclear Overhauser effect ; bioactive peptides ; Chemistry ; Organic Chemistry
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Notes: A modern method is reported for the assignment of absolute configuration for peptidomimetics in bioactive peptides by use of 1H-NMR parameters in solution. Four peptide systems incorporating either retro-inverso modifications or 2-aminocyclopentanecarboxylic acid (2-Ac5c) as a peptidomimetic for proline are discussed. (1) Two 14-membered cyclic dermorphin analogs Tyr-c[D-A2bu-Phe-gPhe-(S and R)-mLeu] with a reverse amide bond between gPhe and mLeu residues where gPhe denotes a gem-diamino analog of Phe and mLeu refers to a malonyl analog of Leu. (2) Two cyclic hexapeptides related to somatostatin, c[gSar6-(S and R)-mPhe7-D-Trp8-Lys9-Thr10-Phe11], with a reverse amide bond between the gSar and mPhe residues where the gSar and mPhe denote the gem-diamino and malonyl analogs of the Sar and Phe residues, respectively. The superscript numbers refer to positions in native somatostatin. (3) Cyclic hexapeptide somatostatin analogs containing 2-Ac5c [trans-(1S,2S)-2-Ac5c, trans-(1R,2R)-2-Ac5c, cis-(1R,2S)-2-Ac5c, and cis-(1S,2R)-2-Ac5c] in place of proline c[(2-Ac5c)6-Phe7-D-Trp8-Lys9-Thr10-Phe11]. (4) Morphiceptin related analogs incorporating a cis-2-Ac5c residue as shown in Tyr-cis-2-Ac5c-Phe-Val-NH2. The methodology described in this investigation could be applied to a wide variety of peptide systems.
    Additional Material: 7 Ill.
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1002/chir.530030410
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  • 3
    Electronic Resource
    Electronic Resource
    Sweet and bitter taste: Structure and conformations of two aspartame dipeptide analogues (1995)
    New York, NY [u.a.] : Wiley-Blackwell
    Journal of Peptide Science 1 (1995), S. 349-359 
    Details
    ISSN: 1075-2617
    Keywords: X-ray structures ; conformational analysis ; taste ligands ; peptidomimetics ; sweetener ; Chemistry ; Biochemistry and Biotechnology
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Notes: The synthesis and X-ray diffraction analysis of two dipeptide taste ligands have been carried out as part of our study of the molecular basis of taste. The compounds L-aspartyl-D-α-methylphenylalanine methyl ester [L-Asp-D-(αMe)Phe-OMe] and L-aspartyl-D-alanyl-2,2,5,5-tetramethylcyclopentanyl ester [L-Asp-D-Ala-OTMCP] elicit bitter and sweet taste, respectively. The C-terminal residues of the two analogues adopt distinctly different conformations in the solid state. The aspartyl moiety assumes the same conformation found in other dipeptide taste ligands with the side-chain carboxylate and the amino groups formaing a zwitterionic ring with a conformation defined by ψ,χX1 = 157.7°, -61.5° for L-Asp-D-Ala-OTMCP and 151.0°, -68.8° for L-Asp-D-(αMe)Phe-OMe. In the second residue, a left-handed helical conformations is observed for the (αMe)Phe residue of L-Asp-D-(αMe)Phe-OMe with φ2 = 49.0° and ψ2 = 47.9°, while the Ala residue of L-Asp-D-Ala-OTMCP adopts a semi-exextended conformation characterized by dihedral angles φ2 = 62.8° and ψ2 = -139.9°. The solid-state structure of the bitter L-Asp-D-(αMe)Phe-OMe is extended; while the crystal structure of the sweet L-Asp-D-OTMCP roughly adopts the typical L-shaped structure shown by other sweeteners. The data of L-Asp-D-(αMe)Phe-OMe are compared with those of its diastereoisomer L-Asp-L-(αMe)Phe-OMe. Conformational analysis of the two taste ligands in solution by NMR and computer simulations agrees well with our model for sweet and bitter tastes.
    Additional Material: 6 Ill.
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1002/psc.310010602
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  • 4
    Electronic Resource
    Electronic Resource
    β,β-Dimethylcyclolanthionines, New Constrained Dipeptide Mimetics: Synthesis, Crystal Structures, and Conformational StudiesWe thank Drs. George Ösapay (UC-Riverside), Yunfei Zhu (Bioresearch Inc.), and Joseph Taulane for helpful discussions. We also thank Dr. Richard Kondrat (UC-Riverside) for mass spectroscopic analyses. This work was supported by the NIH (grant DK-15410).Dedicated to Professor Ivar Ugi on the occasion of his 65th birthday (1996)
    Weinheim : Wiley-Blackwell
    Angewandte Chemie International Edition in English 35 (1996), S. 90-92 
    Details
    ISSN: 0570-0833
    Keywords: lanthionines ; peptidomimetics ; Chemistry ; General Chemistry
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Additional Material: 2 Ill.
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1002/anie.199600901
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