Water-induced switching of beta-structure to polyproline II conformation in the 4s-aminoproline polypeptide via H-bond rearrangement
| Title | Water-induced switching of beta-structure to polyproline II conformation in the 4s-aminoproline polypeptide via H-bond rearrangement |
| Publication Type | Journal Article |
| Year of Publication | 2010 |
| Authors | Sonar, MV, Ganesh, KN |
| Journal | Organic Letters |
| Volume | 12 |
| Issue | 23 |
| Pagination | 5390-5393 |
| Date Published | DEC |
| ISSN | 1523-7060 |
| Abstract | 4S-Aminoproline polypeptide 2 forms unusual beta-structure in trifluoroethanol that switches to the polyproline II (PPII) form in aqueous medium. while 4R-aminoproline peptide 1 retains PPII form in both solvents. This first instance of a polyproline derivative showing a beta-structure is attributed to competitive pH-dependent (4-NH3+/NH2) stereoelectronic effect (4R vs 4S) and the overriding importance of stercospecific intra/intermolecular H-bonding in (2,4)-cis-4S-aminoproline in contrast to (2,4)-trans-4R-aminoproline oligomers. |
| DOI | 10.1021/ol1021993 |
| Type of Journal (Indian or Foreign) | Foreign |
| Impact Factor (IF) | 5.250 |
Divison category:
Organic Chemistry