| Full text | |
| Author(s): |
Soares, B. M.
;
Aguilar, A. M.
;
Silva, E. R.
;
Coutinho-Neto, M. D.
;
Hamley, I. W.
;
Reza, M.
;
Ruokolainen, J.
;
Alves, W. A.
Total Authors: 8
|
| Document type: | Journal article |
| Source: | Physical Chemistry Chemical Physics; v. 19, n. 2, p. 1181-1189, 2017. |
| Web of Science Citations: | 7 |
| Abstract | |
A comprehensive study of the self-assembly in water of a lipopeptide consisting of a sequence of L-proline, L-arginine and L-tryptophan with a hydrocarbon chain has been performed. Fluorescence assays were used to determine the critical aggregation concentration. In situ small-angle X-ray scattering (SAXS) and molecular dynamics simulations showed the presence of spherical micelles with diameters around 6 nm. In agreement with these results, cryo-TEM images showed globular aggregates with diameters ranging from approximate to 4 nm up to approximate to 9 nm. Furthermore, the lipopeptide catalytic activity has been tested for the direct aldol reaction between cyclohexanone and p-nitrobenzaldehyde, and we have observed that the self-association of the organocatalyst played a critical role in the enhanced activity. Water affects the selectivity, and poor results are obtained under neat reaction conditions. The location of the catalytic groups at the lipopetide/ water solvent interface also endowed unusual selectivity in the catalyzed aldol reactions. Under optimized reaction conditions, high yields (up to >99%), good enantioselectivity (ee up to 85%) and high diastereoselectivity (ds up to 92 : 8) were obtained. (AU) | |
| FAPESP's process: | 15/24018-1 - Polymer-Peptide Conjugates for hydrogel formulation and its usage in detection |
| Grantee: | Wendel Andrade Alves |
| Support Opportunities: | Regular Research Grants |
| FAPESP's process: | 08/57805-2 - Institute of Bioanalytics |
| Grantee: | Lauro Tatsuo Kubota |
| Support Opportunities: | Research Projects - Thematic Grants |
| FAPESP's process: | 13/12674-6 - Structural investigations on model systems based on amphiphilic peptides |
| Grantee: | Emerson Rodrigo da Silva |
| Support Opportunities: | Scholarships in Brazil - Post-Doctoral |