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From Structure to Function: From the Development of a Curved Hetero-Oligomer to the Development of an Actuated Glucose Sensor

Morgan, Christopher William (2007) From Structure to Function: From the Development of a Curved Hetero-Oligomer to the Development of an Actuated Glucose Sensor. Master's Thesis, University of Pittsburgh. (Unpublished)

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The Schafmeister research group has developed a technology for synthesizing bis-peptide oligomers that adopt well defined structure dependent upon the rich stereochemistry of the independent bis-amino acid monomers used in its construction. These bis-amino acid monomers are designed to construct rigid bis-peptide scaffolds by utilizing a pair of amide bonds that form a 2,5 diketopiperazine (DKP) ring linkage between two monomers. It is hoped to be able to precisely position functionality within our rigid scaffolds so as to allow us to explore potential applications with our bis-peptide oligomers. Developing new bis-amino acid monomers will help achieve this goal. The first part of this thesis outlines the synthesis of the pip5(2R5R) and pip5(2R5S) bis-amino acid monomers. The newly synthesized pip5(2R5S) monomer was then coupled into a bis-peptide sequence with the previously synthesized pip5(2S5R) monomer. Molecular modeling predicted that this particular sequence formed a tight turn in space; a useful structural motif for the exploration of small cavities and clefts. The solution structure of this bis-peptide oligomer was determined by 2D-NMR techniques including a ROESY to determine important close contact information between protons on the same monomer and protons on adjacent monomers. In addition, two powerful 2D-NMR techniques that have begun their integration into our lab for structure determination were used to provide more NMR restraints on the bis-peptide structural model. These included amplitude-constrained multiplet evaluation of 3JHH coupling constants and the use of residual dipolar coupling (RDC) constants. Lastly, I have recently begun work on synthesizing a glucose sensitive molecular actuator. This molecular actuator is a water-soluble rod-hinge-rod motif that converts from its disordered "open" form to an ordered "closed" form upon reversible binding to glucose through the 4,6 and 1,2 diol pairs. It is envisioned that these rod-hinge-rod motifs can eventually be used for potential applications such as nanovalves.


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Item Type: University of Pittsburgh ETD
Status: Unpublished
CreatorsEmailPitt UsernameORCID
Morgan, Christopher Williamcwm8@pitt.eduCWM8
ETD Committee:
TitleMemberEmail AddressPitt UsernameORCID
Committee ChairSchafmeister, Christianmeister@pitt.eduMEISTER
Committee MemberWilcox, Craigdaylite@pitt.eduDAYLITE
Committee MemberCurran, Denniscurran@pitt.eduCURRAN
Date: 14 June 2007
Date Type: Completion
Defense Date: 6 December 2006
Approval Date: 14 June 2007
Submission Date: 10 April 2007
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: MS - Master of Science
Thesis Type: Master's Thesis
Refereed: Yes
Uncontrolled Keywords: Bis-amino acids; glucose binding; glucose sensing; macromolecules; NMR techniques; residual dipolar coupling
Other ID:, etd-04102007-164326
Date Deposited: 10 Nov 2011 19:35
Last Modified: 15 Nov 2016 13:39


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