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  • 1
    Electronic Resource
    Electronic Resource
    Synthesis of Combinatorial Libraries of Vinylogous Sulfonamidopeptides (vs-Peptides) (1998)
    Weinheim : Wiley-Blackwell
    Liebigs Annalen 1998 (1998), S. 2437-2449 
    Details
    ISSN: 1434-193X
    Keywords: Vinylogous sulfonamidopeptides ; Solid-phase synthesis ; Combinatorial libraries ; N-Alkylation ; Michael addition ; Chemistry ; General Chemistry
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Notes: Chiral vinylogous sulfonamidopeptides (vs-peptides) were synthesized on TentaGel resin employing (S)- and (R)-N-Boc-vinylogous sulfonyl chlorides 2a-i as building blocks. Glycine and two different photocleavable molecules were used as linkers, and the corresponding cleavage conditions were optimized. According to preliminary studies in solution and on solid phase, three libraries were synthesized with the “split-mix synthesis” method. Taking advantage of the acidic character of the sulfonamides (RSO2-NHR: pKa = 10-11), mild conditions were developed to alkylate the sulfonamide nitrogen atom so as to reduce the acidity of the monomers and of the oligomers and increase their in vivo bioavailability. This synthetic methodology was employed to increase the diversity in a library of di-N-alkylated vs-dipeptides 26. The electron-withdrawing capability of the sulfonamido group pointed to the use of vinylogous sulfonamidopeptides as Michael acceptors. The sodium enolate of dimethyl malonate was used as nucleophile to obtain N-Boc-γ-lactams 35 in moderate yields and good diastereoselectivity.
    Additional Material: 3 Ill.
    Type of Medium: Electronic Resource
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  • 2
    Electronic Resource
    Electronic Resource
    Solid-Phase Synthesis of Peptides Containing Reverse-Turn Mimetic Bicyclic Lactams (1999)
    Weinheim : Wiley-Blackwell
    Liebigs Annalen 1999 (1999), S. 379-388 
    Details
    ISSN: 1434-193X
    Keywords: Solid-phase synthesis ; Reverse-turns ; FMOC strategy ; Peptidomimetics ; Chemistry ; General Chemistry
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Notes: -The solid-phase synthesis and characterization of a series of peptides (4-15) containing reverse-turn mimetic bicyclic lactams is reported. The bicyclic lactams (1a, 1b) possess high structural similarity to the two central residues of a β-turn. Amino acid conjugates of these bicyclic lactams were synthesized on solid supports following a 9-fluorenylmethoxycarbonyl (FMOC) protection strategy on Wang-Merrifield resin. Coupling between amino acids was accomplished by means of diisopropylcarbodiimide (DIC)/hydroxyazabenzotriazole (HOAt). Coupling between amino acids and the mimics was performed with the potent Carpino's reagent O-(7-azabenzotriazol-1-yl)-N,N,N′,N′-tetramethyluronium hexafluorophosphate (HATU). The final compounds were cleaved from the resin and obtained as N-acetylated methyl esters or benzyl amides.Supporting information for this article is available on the WWW under -http://www.wileY-Vch.de/contents/jc_2046/1999/98399_s.pdf or from the author.
    Additional Material: 5 Ill.
    Type of Medium: Electronic Resource
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