Peptides as Modular Scaffolds for Molecular Recognition
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Home > Mathematics and Science books > Chemistry > Peptides as Modular Scaffolds for Molecular Recognition
Peptides as Modular Scaffolds for Molecular Recognition

Peptides as Modular Scaffolds for Molecular Recognition


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About the Book

Two approaches using chemically modified peptides to gain insights into molecular recognition are detailed. Due to synthetic inefficiency and a propensity toward multiple conformations, cyclic tetrapeptides have gone largely unstudied in the field of medicinal chemistry despite known cases of potent medicinal activity in isolated natural products. By including a single beta-amino acid into the backbone of the structure, or replacing amide bonds with 1,2,3-triazole surrogates, cyclic tetrapeptides are shown to become attainable synthetic targets that typically exhibit a single conformation on the nuclear magnetic resonance timescale. In Part I of this thesis, exploration into the structural similarities and differences of 1,4-disubstituted-1,2,3-triazoles, and 1,5-disubstituted-1,2,3-triazoles, as respective trans and cis amide bond mimics is detailed in an approach to better understanding the active conformation of a known cyclic tetrapeptide histone deacetylase inhibitor apicidin. Further study probing the implications of these cyclic scaffolds as beta-turn mimetics toward the biological target of somatostatin is detailed. In Part II of the thesis, linear poly-cysteine peptides are shown to be capable of engaging in dynamic covalent chemistry with thioester functionalized nucleobase derivatives. This thiopeptide nucleic acid (tPNA) system shows a remarkable ability to undergo enzyme free constitutional modifications in the presence of a changing environment. The use of template directed synthesis under dynamic equilibrium conditions show the tPNA system can be subjected to thermodynamic control allowing sequence specific alterations to take place solely by changing the identity of different oligonucleotide templates. A mechanistic study is further detailed using a tPNA-DNA chimera detailing insights into error correction and read length mechanisms in a four nucleobase system.


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Product Details
  • ISBN-13: 9781243627414
  • Publisher: Proquest, Umi Dissertation Publishing
  • Publisher Imprint: Proquest, Umi Dissertation Publishing
  • Height: 254 mm
  • Weight: 621 gr
  • ISBN-10: 1243627417
  • Publisher Date: 01 Sep 2011
  • Binding: Paperback
  • Spine Width: 21 mm
  • Width: 203 mm


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