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  • 1
    Electronic Resource
    Electronic Resource
    Springer
    International journal of peptide research and therapeutics 5 (1998), S. 175-178 
    ISSN: 1573-3904
    Keywords: antibiotic ; isotope labeling ; peptaibol ; peptidesynthesis
    Source: Springer Online Journal Archives 1860-2000
    Topics: Chemistry and Pharmacology
    Notes: Abstract Synthesis of zervamicin IIB, specifically labeled at the α-position of glutamine-11 with 15N, was achieved by the Fmoc/tert.-butyl strategy in solution using a fragment condensation approach. Three fragments of zervamicin IIB were obtained by stepwise elongation with Fmoc amino acids using BOP as a coupling reagent. For the introduction of the highly sterically hindered α-aminoisobutyric acid residues, BOP/DMAP activation was applied. Peptide fragments were coupled by means of the coupling reagent, CF3-PyBOP. Using the strategy developed, zervamicin IIB specifically 15N labeled has been synthesized in 30% overall yield based on the isotopically labeled amino acid. From 600 MHz NMR spectroscopy the position of the 15N-label was clearly detected. The isotope enrichment (98 ± 2%) was determined by FAB-mass spectrometry.
    Type of Medium: Electronic Resource
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  • 2
    Electronic Resource
    Electronic Resource
    Springer
    International journal of peptide research and therapeutics 5 (1998), S. 175-178 
    ISSN: 1573-3904
    Keywords: antibiotic ; isotope labeling ; peptaibol ; peptide synthesis
    Source: Springer Online Journal Archives 1860-2000
    Topics: Chemistry and Pharmacology
    Notes: Summary Synthesis of zervamicin IIB, specifically labeled at the α-position of glutamine-11 with15N, was achieved by the Fmoc/tert.-butyl strategy in solution using a fragment condensation approach. Three fragments of zervamicin IIB were obtained by stepwise elongation with Fmoc amino acids using BOP as a coupling reagent. For the introduction of the highly sterically hindered α-aminoisobutyric acid residues, BOP/DMAP activation was applied. Peptide fragments were coupled by means of the coupling reagent, CF3-PyBOP. Using the strategy developed, zervamicin IIB specifically15N labeled has been synthesized in 30% overall yield based on the isotopically labeled amino acid. From 600 MHz NMR spectroscopy the position of the15N-label was clearly detected. The isotope enrichment (98 ±2%) was determined by FAB-mass spectrometry.
    Type of Medium: Electronic Resource
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  • 3
    Electronic Resource
    Electronic Resource
    Weinheim : Wiley-Blackwell
    Liebigs Annalen 2000 (2000), S. 857-859 
    ISSN: 1434-193X
    Keywords: α,α-Dialkylated amino acids ; Isotopic labeling ; Strecker synthesis ; Solvent effects ; Stereoselective hydrolysis ; Chemistry ; General Chemistry
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Notes: ---[15N]-D-isovaline was prepared from DL-[α-15N]-α-aminoisovaleramide by enzymatic resolution with Mycobacterium neoaurum. The 15N-isotope was introduced during the Strecker synthesis of its precursor, e.g. aminoisovaleronitrile. Attempts to prepare the amino nitrile precursor of [15N]-α-aminoisobutyric acid (Aib) led to a poor yield and loss of the label. Significantly, improved results were obtained when a cosolvent is present during formation of aminoisobutyronitrile.
    Additional Material: 1 Ill.
    Type of Medium: Electronic Resource
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