[2 + 2] Photocycloadditions with Chiral Uracil Derivatives: Access to All Four Stereoisomers of 2-Aminocyclobutanecarboxylic Acid
| Autor: | Elisabeth Pereira, Olivier Roy, Carlos Fernandes, Sophie Faure, Yi Yang, Christine Gauzy, David J. Aitken |
|---|---|
| Přispěvatelé: | Synthèse et étude de systèmes à intêret biologique (SEESIB), Université Blaise Pascal - Clermont-Ferrand 2 (UBP)-Institut de Chimie du CNRS (INC)-Centre National de la Recherche Scientifique (CNRS), Université Blaise Pascal - Clermont-Ferrand 2 (UBP)-Centre National de la Recherche Scientifique (CNRS)-Institut de Chimie du CNRS (INC) |
| Jazyk: | angličtina |
| Rok vydání: | 2007 |
| Předmět: |
Stereochemistry
Sequence (biology) 02 engineering and technology 010402 general chemistry 01 natural sciences Catalysis 03 medical and health sciences chemistry.chemical_compound Alicyclic compound [CHIM]Chemical Sciences ComputingMilieux_MISCELLANEOUS 030304 developmental biology chemistry.chemical_classification Oligopeptide 0303 health sciences Bicyclic molecule 010405 organic chemistry Organic Chemistry Foldamer Uracil General Medicine 021001 nanoscience & nanotechnology 0104 chemical sciences Amino acid Folding (chemistry) chemistry Nucleic acid 0210 nano-technology |
| Zdroj: | ChemInform ChemInform, 2007, 38 (47), ⟨10.1002/chin.200747068⟩ ChemInform, Wiley-VCH Verlag, 2007, 38 (47), ⟨10.1002/chin.200747068⟩ |
| ISSN: | 0931-7597 1522-2667 |
| DOI: | 10.1002/chin.200747068⟩ |
| Popis: | Starting from a single, chiral, bicyclic derivative of uracil, all four stereoisomers of 2-aminocyclobutanecarboxylic acid have been prepared in enantiomerically pure form, using a synthetic sequence which begins with a key photochemical (2+2) cycloaddi- tion reaction and includes a practical cis to trans b-amino acid isom- erisation procedure. The impact of b-amino acids and b-peptides in nature, 1 in medicinal chemistry, 2 and in the controlled design of pep- tide folding structures 3 is evident from the exponential in- crease in the volume of published research on these substances. 4 Commensurately, an increasing variety of methods have been described for the synthesis of b-amino acids in both racemic and enantiomerically enriched form. 5 A particular interest has developed for alicyclic b- amino acids; 6 these compounds are of biological interest in their own right, 6,7 while hybrid or homo-oligomers which contain these rigid cyclic motifs pre-organize in a well-defined manner leading to unique 'foldamer' struc- tures. Thus, stable helical motifs have been prepared using oligomers of trans-2-aminocyclohexanecarboxylic acid 8 and trans-2-aminocyclopentanecarboxylic acid, 8b,9 and some of these oligopeptides are bestowed with biological activities 10 or liquid crystal properties. 11 In marked con- trast, oligomers of cis-2-aminocyclopentanecarboxylic acid adopt a sheet-like structure. 12 Much less work has been done using small-ring b-amino acids, although initial results have been promising: for example, cis-2-aminocy- clopropanecarboxylic acid derived oligopeptides adopt stable helical conformations. 13 In the only studies involv |
| Databáze: | OpenAIRE |
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