Synthesis and structural characterization of homochiral homo-oligomers of parent CIS- and trans-furanoid-beta-amino acids
| Title | Synthesis and structural characterization of homochiral homo-oligomers of parent CIS- and trans-furanoid-beta-amino acids |
| Publication Type | Journal Article |
| Year of Publication | 2011 |
| Authors | Pandey, SK, Jogdand, GF, Oliveira, JCA, Mata, RA, Rajamohanan, PR, Ramana, CV |
| Journal | Chemistry-A European Journal |
| Volume | 17 |
| Issue | 46 |
| Pagination | 12946-12954 |
| Date Published | NOV |
| ISSN | 0947-6539 |
| Keywords | ab initio calculations, Amino acids, Density functional calculations, Peptides, secondary structures |
| Abstract | The synthesis of homochiral homo-oligomers of cis- and trans-3-aminotetrahydrofuran-2-carboxylic acids (parent cis- and trans-furanoid-beta-amino acids, referred to as ``cis-/trans-FAA'') has been carried out to understand their secondary structures and their dependence on the ring heteroatom. The oligomers of two diastereomers have been shown to have a distinct left-handed helicity. The cis-FAA homo-oligomers show a 14-helix structure, in contrast to the homo-oligomers of cis-ACPC, which adopt a sheet like structure. The trans-FAA homo-oligomers were found to adopt a 12-helix structure, the same trend found in trans-ACPC homo-oligomers. With the help of ab initio calculations, the structural features of cis-ACPC and cis-FAA hexamers were compared. We believe that the more compact packing of the cis-FAA hexapeptide should be due to a more favorable interaction between the ring and the backbone amide hydrogen. |
| DOI | 10.1002/chem.201101855 |
| Type of Journal (Indian or Foreign) | Foreign |
| Impact Factor (IF) | 5.81 |