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    Syntheses of Silanediol Amino acids and alpha-amino-alpha-alkylsilanediol precursors

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    Genre
    Thesis/Dissertation
    Date
    2008
    Author
    Kim, Jin Kyung
    Advisor
    Sieburth, Scott McNeill
    Committee member
    Williams, John R.
    Davis, Franklin A.
    Berry, Donald H.
    Department
    Chemistry
    Subject
    Chemistry, Organic
    Silanediol
    Aziridine
    Aminosilane
    Protease Inhibitors
    Organosilane
    Permanent link to this record
    http://hdl.handle.net/20.500.12613/3719
    
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    DOI
    http://dx.doi.org/10.34944/dspace/3701
    Abstract
    Two research projects are described: studies of the synthesis of alpha-amino-alpha-alkylsilanes, the synthetic precursor of silanediol-based protease inhibitors, and the synthesis and stability evaluation of silanediol amino acids with an unprecedently unhindered silanediol group. Two methods were investigated as approaches to alpha-amino-alpha-alkylsilanes. First, a silicon-substituted aziridine was chosen as the precursor of an alpha-amino-alpha-alkylsilane via ring opening reactions with carbon nucleophiles. Silyl-substituted aziridines 2-24 and 2-30 were prepared via direct lithiation/silylation of aziridine and employed as substrates for ring opening reactions. In spite of many attempts to ring open these silylaziridines and prepare ?-amino-?-alkylsilanes, optimization of the reaction conditions were unsuccessful. Secondly, alpha-chloro-alpha-benzylsilane 3-12 was prepared as the precursor of an alpha-amino-alpha-alkylsilane via lithiation/benzylation. The alkylation at carbon alpha to silicon to give chloromethylsilane 3-14 was successful when using n-butyllithium for lithiation, which could be explained by the steric encumbrance inherent in the structure. Several attempts for nucleophilic displacement of chloride to obtain alpha-chloro-alpha-benzylsilane 3-11 were unsuccessful possibly due to the steric effect as well as the electronic effect of silicon on the alpha carbon which made the chloride less reactive toward nucleophilic substitution. The silanediol amino acid 4-1 was synthesized originally as a potential arginase inhibitor. Although the expected biological activity was not observed, the studies on silanediol-siloxane distribution of the silanediol amino acid revealed the unique properties of this compound. Under basic conditions, the silanediol amino acid was mainly stable in monomeric form. As the pH decreased, the silanediol amino acid gave a mixture of siloxanes which consisted of a variety of stereoisomers. With available instrumental techniques, monomer, dimers and trimers of the silanediol amino acid were identified.
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