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Home > Mathematics and Science books > Chemistry > Part I
Part I

Part I


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About the Book

Part I. Bullvalene is a ten-carbon molecule whose unique bonding pattern endows it with the intriguing ability to spontaneously alter its molecular arrangement through degenerate strain-assisted Cope rearrangements. Hypothesizing that this fluxional molecule could be elaborated to form an adaptive organic molecule capable of responding to external stimuli, an efficient ten-step synthetic route, featuring a key intramolecular cyclopropanation of a novel sulfur ylide, to yield a tetrasubstituted bullvalene has been developed. Elaborate functionality, such as porphyrins, was incorporated onto this shape shifting scaffold using cross metathesis. Cope rearrangements of the bullvalene core allow these molecules to exist in a dynamic equilibrium of more than 800 constitutional isomers. Explorations into the interaction of the shape shifting bisporphyrin bullvalene with C60 have revealed an active network of interconverting species that appear to adapt to more tightly bind to the molecular guest. Part II. In order for the novel decarboxylative amide forming reaction between alpha-ketoacids and hydroxylamines to find use as a practical method for peptide ligation, it is crucial to have facile methods to install these functionalities onto the C-terminus and N-terminus of peptides. The preparation of C-terminal peptidic alpha-ketoacids has been accomplished through the mild oxidation of bench stable peptidic cyanosulfur ylides. The cyanosulfur ylides can be readily prepared using standard peptide coupling conditions and the oxidation conditions are compatible with most amino acid side chains. In addition, a highly chemoselective method for the production of N-terminal glycine hydroxylamines has been established through a short sequence of orthogonal reactions, including a chemospecific oxidation of an N-terminal glycine, oxime formation, and selective reduction. This method can be utilized on completely unprotected peptides.


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Product Details
  • ISBN-13: 9781243591890
  • Publisher: Proquest, Umi Dissertation Publishing
  • Publisher Imprint: Proquest, Umi Dissertation Publishing
  • Height: 246 mm
  • Weight: 590 gr
  • ISBN-10: 1243591897
  • Publisher Date: 01 Sep 2011
  • Binding: Paperback
  • Spine Width: 18 mm
  • Width: 189 mm


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