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- W761583100 abstract "A major goal of peptide research has been to elucidate or understand the relationships between a peptide's three-dimensional structure and its biological activity. De Novo design of peptide mimetics requires assembling all components necessary for molecular recognition and transduction, which needs the proper choice of a template that can place the key side chain residues in 3D space. Two widely used methods are novel P-substituted amino acids and conformationally constrained secondary structure mimetics. In this thesis, we report our efforts to fiilfill the aforementioned criteria in synthesizing P-isopropyl aromatic amino acids and constrained reverse turn dipeptide mimetics. Through asymmetric Michael addition reaction, highly topographically constrained P-isopropyl aromatic amino acids have been synthesized. In order to develop a general approach to synthesize these novel amino acids, we re-examined the reaction conditions for Evans' diastereoselective 1,4-addition, and found conditions which gave excellent diastereoselectivities and good chemical yields. A concise and straightforward five-step synthesis of [5.5]-bicyclic reverse tum dipeptide mimetic scaffolds with side chain functionality at the /-i-1 and i+2 positions has been developed. In the bicyclic structure, two dihedral angles (i(/2 and ({)3) are greatly restricted. Further development of this synthesis will enable us to prepare various types of reverse turns with different backbone geometry and side chain topography. Enantiomerically pure (51-rra«5-cinnamylglycine and (5)-a-rra/25-cinnamyl-aalanine have been prepared via reaction of chiral Ni (Il)-complexes of glycine and alanine respectively, with cinnamyl halides. Inexpensive and readily available reagents and solvents are used, including a recyclable chiral ligand. The simplicity of the" @default.
- W761583100 created "2016-06-24" @default.
- W761583100 creator A5083172064 @default.
- W761583100 date "2001-01-01" @default.
- W761583100 modified "2023-09-27" @default.
- W761583100 title "Design and synthesis of conformationally and topographically constrained amino acids as peptidomimetics" @default.
- W761583100 hasPublicationYear "2001" @default.
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