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Peptide and non-peptide mimetics of ...

Mowery, Brendan Patrick.

Peptide and non-peptide mimetics of somatostatin-14 and urotensin II.

Record Type:	Electronic resources : Monograph/item
Title/Author:	Peptide and non-peptide mimetics of somatostatin-14 and urotensin II.
Author:	Mowery, Brendan Patrick.
Description:	427 p.
Notes:	Advisers: Ralph Hirschmann; Amos B. Smith, III.
Notes:	Source: Dissertation Abstracts International, Volume: 67-07, Section: B, page: 3805.
Contained By:	Dissertation Abstracts International67-07B.
Subject:	Chemistry, Organic.
Online resource:	http://pqdd.sinica.edu.tw/twdaoapp/servlet/advanced?query=3225507
ISBN:	9780542799822

Peptide and non-peptide mimetics of somatostatin-14 and urotensin II.
Mowery, Brendan Patrick.

Peptide and non-peptide mimetics of somatostatin-14 and urotensin II. - 427 p.

Advisers: Ralph Hirschmann; Amos B. Smith, III.

Thesis (Ph.D.)--University of Pennsylvania, 2006.

*Please refer to dissertation for diagrams.

ISBN: 9780542799822Subjects--Topical Terms:

193634
Chemistry, Organic.

Peptide and non-peptide mimetics of somatostatin-14 and urotensin II.
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100 0 $a Mowery, Brendan Patrick. $3 264200
245 1 0 $a Peptide and non-peptide mimetics of somatostatin-14 and urotensin II.
300 $a 427 p.
500 $a Advisers: Ralph Hirschmann; Amos B. Smith, III.
500 $a Source: Dissertation Abstracts International, Volume: 67-07, Section: B, page: 3805.
502 $a Thesis (Ph.D.)--University of Pennsylvania, 2006.
520 # $a *Please refer to dissertation for diagrams.
520 # $a Chapter 2 summarizes the design and implementation of monosaccharides as nonpeptide mimetics of SRIF, culminating in the synthesis of (-) -2-37, our highest-affinity SRIF receptor subtype 4 (sst4) ligand to date. The syntheses of (-)-2-37 and C4-pyrazinyl congener (-) -2-42 are described, and collaborators at MDS Pharma Services in Taiwan assayed both at sst4. To understand some previously unexplained SAR data, we then performed T1 relaxation time 13C NMR experiments to determine whether an intramolecular aromatic stacking interaction occurs between the C3 and C4 substituents of the ligand. Because such stacking was not observed, we concluded that any side chain conformation perturbation is most likely induced by the receptor itself. Additionally, the discovery of the catechol scaffold, typified by 2-85, as a minimal peptidomimetic of the i + 1 and i + 2 positions of a beta-turn is described.*
520 # $a Chapter 3 provides a synopsis of the Hirschmann-Smith collaboration's past research into peptide mimetics of SRIF. After describing a practical, scalable synthesis of Nalpha-Fmoc-L -pyrazin-2-ylalanine for our study of the binding conformation of SRIF-14 analogues, the design and synthesis of octapeptide ligands 3-20 through 3-22 is described. Molecular modeling of the electrostatic potential (EP) surfaces of various indole surrogates was performed, and 5-methoxytryptophan and 5-chlorotryptophan were selected as amino acids bearing enhanced and diminished EP surfaces, respectively. Binding studies revealed that the 5-chlorotryptophan analogues exhibited the highest affinities, suggesting that a hydrophobic pi-acceptor is required in the tryptophan binding pocket of the SRIF receptors.
520 # $a Chapter 4 details preliminary studies of monosaccharide-based non-peptide mimetics of urotensin II. Our group's previous synthesis of 4-5, a potent cyclic hexapeptide agonist of U-II, is summarized. The influence of those results and the scaffold's radial symmetry on the design of glucoside ligand (-)-4-11 and glucal derivatives (-)-4-16 and 4-17 is described.*
520 # $a This dissertation describes the design and synthesis of peptide- and monosaccharide-based peptidomimetics for the somatostatin (SRIF) and urotensin II (U-II) receptors. The introductory chapter provides background on the pharmacology of the somatostatin and urotensin II receptors and a brief summary of previously published work on peptide and non-peptide mimetics of SRIF and urotensin II.
590 $a School code: 0175.
650 # 0 $a Chemistry, Organic. $3 193634
690 $a 0490
710 0 # $a University of Pennsylvania. $3 212781
773 0 # $g 67-07B. $t Dissertation Abstracts International
790 $a 0175
790 1 0 $a Hirschmann, Ralph, $e advisor
790 1 0 $a Smith, Amos B., III, $e advisor
791 $a Ph.D.
792 $a 2006
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