MEDLINE Journals

    Comparison of the effects of 5- and 6-HOAt on model peptide coupling reactions relative to the cases for the 4- and 7-Isomers.

    Authors
    Carpino LA, Imazumi H, Foxman BM, et al. 
    Institution

    Department of Chemistry, University of Massachusetts, Amherst, Massachusetts 01003, USA. carpino@chem.umass.edu

    Source
    Org Lett 2000 Jul 27; 2(15) :2253-6.
    Abstract

    Synthesis of 5- and 6-HOAt has completed the full set of the four HOAt isomers derived from HOBt by insertion of a single nitrogen atom in the benzenoid nucleus. Comparison of the reactivity of all four isomers in model peptide coupling reactions has confirmed the unique character of the 7-isomer in promoting selectivity and maintaining configuration at the reactive carboxylic acid residue.

    Mesh
    Aniline Compounds
    Isomerism
    Kinetics
    Methylation
    Nitrogen
    Peptides
    Triazoles
    Language

    eng

    Pub Type(s)
    Comparative Study Journal Article Research Support, Non-U.S. Gov't Research Support, U.S. Gov't, Non-P.H.S. Research Support, U.S. Gov't, P.H.S.
    PubMed ID

    10930256

    Content Manager
    Related Content

    Oxyma: an efficient additive for peptide synthesis to replace the benzotriazole-based HOBt and HOAt with a lower risk of explosion.

    The 5,6- and 4,5-benzo derivatives of 1-hydroxy-7-azabenzotriazole.

    Organophosphorus and nitro-substituted sulfonate esters of 1-hydroxy-7-azabenzotriazole as highly efficient fast-acting peptide coupling reagents.

    Synthesis of bitriazolyl nucleosides and unexpectedly different reactivity of azidotriazole nucleoside isomers in the Huisgen reaction.

    (1H-benzotriazol-1-yloxy)-N,N-dimethylmethaniminium hexachloroantimonate (BOMI), a novel coupling reagent for solution and solid-phase peptide synthesis.

    Effects of amounts of additives on peptide coupling mediated by a water-soluble carbodiimide in alcohols.

    Linkage isomerism in the binding of pentapeptide Ac-His(Ala)3His-NH2 to (ethylenediamine)palladium(II): effect of the binding mode on peptide conformation.

    Reactions of monoaryl-substituted methylenecyclobutanes and methylenecyclopropanes with 1-hydroxybenzotriazole (HOBt), 1-hydroxy-7-azabenzotriazole (HOAt), and 1-hydroxysuccinimide (HOSu).