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Amide bond cleavage: acceleration due to a 1,3-diaxial interaction with a carboxylic acid.

Amide bond cleavage: acceleration due to a 1,3-diaxial interaction with a carboxylic acid. Research Abstract Details 

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  • Amide bond cleavage: acceleration due to a 1,3-diaxial interaction with a carboxylic acid. Abstract Text:

    jared j gerschlerJared J Gerschler,kevin a wierKevin A Wier,david e hansenDavid E Hansen,

    To independently assess the contribution of ground-state pseudoallylic strain to the enormous rates of amide bond cleavage in tertiary amide derivatives of Kemp's triacid, we have studied four amide derivatives of (1alpha-3alpha-5beta)-5-tert-butyl-1,3-cyclohexanedicarboxylic acid. Our results demonstrate that absent pseudoallylic strain, a 1,3-diaxial interaction of an amide with a carboxylic acid leads to only a 2400-fold increase in the rate of amide bond cleavage as compared with the rate of hydrolysis of an unactivated peptide bond.

    Amide bond cleavage: acceleration due to a 1,3-diaxial interaction with a carboxylic acid. Publishing Authors By Initials

    jj gerschlerJJ Gerschler,ka wierKA Wier,de hansenDE Hansen,

    For similar natural sciences: time: time factors research abstracts see: natural sciences: time: time factors research

    PUBMED ID PMID:

    MEDLINE DATE:

    Amide bond cleavage: acceleration due to a 1,3-diaxial interaction with a carboxylic acid. Journal Published:

    PUBLICATION TYPE: Research Support, Non-U.S. Gov

    Journal: The Journal of organic chemistry

    VOLUME: 72

    Page Numbers: 654-7

    Journal Abbreviation: J. Org. Chem.

    ISSN: 0022-3263

    DAY: 19

    MONTH: Jan

    YEAR: 2007

    Amide bond cleavage: acceleration due to a 1,3-diaxial interaction with a carboxylic acid. Information

    Number of References:

    LANGUAGE: eng

    NlmUniqueID: 2985193

    Amide bond cleavage: acceleration due to a 1,3-diaxial interaction with a carboxylic acid. Keywords Mesh Terms:

    KEYWORDS: Time Factors

    MESH TERMS: chemistry

    Chemical & Substance for Abstract: Amide bond cleavage: acceleration due to a 1,3-diaxial interaction with a carboxylic acid. Information

    Substance Name: Carboxylic Acids

    Registry Number: 0

    Grant and Affiliation Information for Amide bond cleavage: acceleration due to a 1,3-diaxial interaction with a carboxylic acid.

    AFFILIATION: Department of Chemistry, Amherst College, Amherst, Massachusetts 01002, USA.

    Country: United States

    United States Research PublicationUnited States Research Publication

    AGENCY: United States NIGMS

    GRANT: R15 GM63776

    ACRONYM: GM

    MEDLINETA: J Org Chem

    REFSOURCE:

    DATABASENAME:

    ACCESSION NUMBER:

    Number Hits: 0

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