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Applications of bis-amino acid oligomers

Bird, Gregory H. (2009) Applications of bis-amino acid oligomers. Doctoral Dissertation, University of Pittsburgh. (Unpublished)

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The ability to precisely position functionality in three-dimensional space is a long term goal for our group. Some progress has been made so far. Using oligomers of our bis-amino acids, we are able to control the distance between two groups, ranging from 2-4nm. Also we are able to control shape and curvature by incorporating monomers that make bends or kinks. There are many potential applications. Some of the most powerful are described in the following pages. We have made a bivalent ligand for Cholera Toxin varying the number of monomers and found that all bivalent molecules that bind more tightly than the natural ligand GM1. The oligomeric scaffold is rigid and the linker contains about 5 rotatable bonds. We have made bivalent vancomycins and bivalent D-Ala-D-Ala, each consisting of linkers of between 1-6 building blocks. These molecules should be capable of associating into matched or mismatched bivalent pairs. In addition, we have made large macrocycles capable of forming a binding pocket. Ligands for these receptors will be identified using phage display. Also, our rigid chiral scaffolds have been studied to determine the influence of chirality on the efficiency of electron transfer. Finally, a scaffold detergent was synthesized, with the application of solubilization of membrane proteins in mind. These are all promising applications of our unique technology and will be explored further in the future.


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Item Type: University of Pittsburgh ETD
Status: Unpublished
CreatorsEmailPitt UsernameORCID
Bird, Gregory
ETD Committee:
TitleMemberEmail AddressPitt UsernameORCID
Committee ChairSchafmeister, Christianmeister@pitt.eduMEISTER
Committee MemberWaldeck, Daviddave@pitt.eduDAVE
Committee MemberCascio, Michaelcascio@pitt.eduCASCIO
Committee MemberWeber, Stevensweber@pitt.eduSWEBER
Date: 10 February 2009
Date Type: Completion
Defense Date: 25 April 2006
Approval Date: 10 February 2009
Submission Date: 27 April 2006
Access Restriction: No restriction; Release the ETD for access worldwide immediately.
Institution: University of Pittsburgh
Schools and Programs: Dietrich School of Arts and Sciences > Chemistry
Degree: PhD - Doctor of Philosophy
Thesis Type: Doctoral Dissertation
Refereed: Yes
Uncontrolled Keywords: bivalent display; electron spin resononance; electron transfer; multivalent interactions; nanotechnology; phage display; vancomycin
Other ID:, etd-04272006-223411
Date Deposited: 10 Nov 2011 19:42
Last Modified: 15 Nov 2016 13:42


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