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Synthesis and NMR Strcuture Determination of Bis-Amino-Acid Oligomers

Morgan, Paul M (2008) Synthesis and NMR Strcuture Determination of Bis-Amino-Acid Oligomers. Doctoral Dissertation, University of Pittsburgh. (Unpublished)

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in chapters 2 and 3, I present the synthesis of three bis-amino acid monomers. The pro3 class of monomers were designed to create a sharp turn in a bis-amino acid oligomeric sequences. The pro3(2S4S) monomer was synthesised, but had an unexpected tendency to epimerize when incorporated into an oligomer. The syntheses of two pip5 class monomers were completed in 13% overall yield and 21% overall yield.In the fourth chapter, I present the first use of residual dipolar coupling (RDC)measurement in the solution structure determination of a bis-amino-aicd oligomer. This technique allows the determination of bond orientations within a molecule with respect to the magnetic field of a nuclear magnetic resonance (NMR)spectrometer. I determined that the information gained from the measurement of RDCs can be used to filter a library of conformational models to select the best fit model to the RDC data. The best fit model was found to ve the lowest energy conformation of the bis-amino acid oligomer.


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Item Type: University of Pittsburgh ETD
Status: Unpublished
CreatorsEmailPitt UsernameORCID
Morgan, Paul
ETD Committee:
TitleMemberEmail AddressPitt UsernameORCID
Committee ChairSchafmeister, Christianmeister@pitt.eduMEISTER
Committee MemberGronenborn, Angela
Committee MemberSpence, Megan
Committee MemberFloreancig, Paul
Date: 28 January 2008
Date Type: Completion
Defense Date: 8 August 2006
Approval Date: 28 January 2008
Submission Date: 6 August 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: PhD - Doctor of Philosophy
Thesis Type: Doctoral Dissertation
Refereed: Yes
Uncontrolled Keywords: Bis-Amino acid; NMR; residual dipolar coupling
Other ID:, etd-08062007-085555
Date Deposited: 10 Nov 2011 19:57
Last Modified: 15 Nov 2016 13:48


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