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• W921634547 abstract "This thesis dealt with the properties of nucleobase-functionalized peptides. Influences of aromatic sidechains on the structure and aggreagation of peptides could be shown. The knowledge about nucleoamino acids, nucleotides and amino acid mimetica gives the opportunity to implement them in various natural and synthetic protein and peptide structures. The substitution by these elements leads to new and promising properties which might allow interactions with DNA and RNA, since various forces like hydrogen bondings, hydrophobic, and electrostatic interactions are involved. Different Boc-protected Alanyl- and Homoalanyl-nucleoamino acids and Fmoc-protected Alanyl- and Homoalanyl-nucleoamino acids were synthesized from enantiomerica lly pure amino acids and amino acid derivatives. The nucleoamino acids were made in both enantiomeric forms due to the necessity of alternating configuration for nucleobase pairings. Oligomerization of the peptide nucleic acids (PNA) from the nucleoamino acids was done by Boc- and Fmoc-solid phase peptide synthesis.Antiparallel PNA double strands were accomplished via covalent binding with a hexaethylene glycol amino acid (hegas)-linker for imitation of the Watson-Crick base pairing. Therefore double strand stabilities of a tetramer and a hexamer were investigated. Oligomerization and the incorporation of the hegas-linker were performed by solid phase peptide synthesis. Stabilities of the tetrameric and hexameric double strands were investigated by temperature-dependent UV spectroscopy and compared to selfpairing oligomers. According to the prospect the hexameric oligomer showed higher pairing stability than the tetrameric oligomer due to the fact the hexameric oligomer can form more base pairs. These linked systems showed less stability compared to the self pairing oligomers that are not additionally stabilized by covalent binding. Reasons for that might be their pairing geometry or alternated recognition possibilities. Higher stabilities could be achieved with more rigid linkers. Therefore various stilben derivates were synthesized starting with 4,4 -trans-stilbendicarboxylate. Activation with SOCl2 leads to three different derivates. Differentiation between both acid chlorid groups turned out to be difficult so that orthogonal functionalized stilbene derivate could not be isolated.Another part of this dissertation dealt with the incorporation of nucleoamino acids in α-helical peptides. Organization and recognition of the nucleobases should lead to a selfpairig of two α-helical strands. The 21-residue and 15-residue systems were analyzed regarding their pairing properties and compared to the nucleobase-modified peptides. Stabilization of the oligomers was accomplished by nucleobase pairing since regular peptides did not show any sigmoidal transition. The 15 residue system gave 10 °C higher stability even though the 21-residue system has two additional basepairs.Another nucleobase-incorporation was performed into the linear micropeptide MCoTi-29. Replacing the arginine unit by the nucleobase guanine gave remaining biological activity meaning that bicyclic heteroaromates with its additional proton-donor-aceptor-functionalties might be an interesting alternative for native peptide- and protein-modifications." @default.
• W921634547 created "2016-06-24" @default.
• W921634547 creator A5066959517 @default.
• W921634547 date "2022-02-20" @default.
• W921634547 modified "2023-09-30" @default.
• W921634547 title "Synthese und Untersuchung von Nukleobasen-funktionalisierten Peptiden" @default.
• W921634547 doi "https://doi.org/10.53846/goediss-2135" @default.
• W921634547 hasPublicationYear "2022" @default.
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