University of Illinois Urbana-Champaign

Synthesis and Properties of Selectively Modifiable Cyclodextrin Analogues

Bodine, Kyle D.

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Description

Title
Synthesis and Properties of Selectively Modifiable Cyclodextrin Analogues
Author(s)
Bodine, Kyle D.
Issue Date
2006
Doctoral Committee Chair(s)
  • Mary S. Gin
  • Gin, David Y.
Degree Granting Institution
University of Illinois at Urbana-Champaign
Degree Name
Ph.D.
Degree Level
Dissertation
Keyword(s)
Chemistry, Organic
Language
eng
Abstract
Cyclodextrins (CDs) are amphiphilic carbohydrate based macrocycles that have been under-utilized in supramolecular chemistry due to difficulties surrounding the selective functionalization of the hydroxyl groups on the macrocycle. A novel strategy for the synthesis of CD analogues is described which involves the use of [3+2] Huisgen cycloadditions between azide and alkyne functionalities to form the macrocycles from linear precursors. This strategy is used in the synthesis of a trisaccharide cyclodimer which was shown to complex a fluorescent dye 8-anilino-1-naphthalene sulfonate with an association constant of 38 +/- 10 M-1. In addition, the synthesis of a monosaccharide cyclotrimer and a disaccharide cyclodimer is presented that were demonstrated to complex 2,4-hexadiyne-1,6-diol with association constants of 8.8 +/- 1.5 M -1 and 10.4 +/- 1.1 M-1, respectively. Alternate synthetic routes which incorporate selectively installed orthogonal protecting groups are discussed for each of the three types of CD analogues. Efforts toward the synthesis of a gated molecular pore are also detailed.
Graduation Semester
2006
Type of Resource
text
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http://hdl.handle.net/2142/87887

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