| Autor: |
Knijnenburg, A.D., Tuin, A.W., Spalburg, E., Neeling, A.J. de, Mars-Groenendijk, R.H., Noort, D., Otero, J.M., Llamas-Saiz, A.L., Raaij, M.J. van, Marel, G.A. van der, Overkleeft, H.S., Overhand, M. |
| Jazyk: |
angličtina |
| Rok vydání: |
2011 |
| Předmět: |
|
| Zdroj: |
Chemistry-A European Journal, 14, 17, 3995-4004 |
| Popis: |
Monobenzylated sugar amino acids (SAAs) that differ in ether ring size (containing an oxetane, furanoid, and pyranoid ring) were synthesized and incorporated in one of the ß-turn regions of the cyclo-decapeptide gramicidin S (GS). CD, NMR spectroscopy, modeling, and X-ray diffraction reveal that the ring size of the incorporated SAA moieties determines the spatial positioning of their cis-oriented carboxyl and aminomethyl substituents, thereby subtly influencing the amide linkages with the adjacent amino acids in the sequence. Unlike GS itself, the conformational behavior of the SAA-containing peptides is solvent dependent. The derivative containing the pyranoid SAA is slightly less hydrophobic and displays a diminished haemolytic activity, but has similar antimicrobial properties as GS. © 2011 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim. |
| Databáze: |
OpenAIRE |
| Externí odkaz: |
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