Leiden Institute of Chemistry, Leiden University, Leiden, The Netherlands.
Chemistry. 2011 Mar 28;17(14):3995-4004. doi: 10.1002/chem.201002895. Epub 2011 Mar 1.
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 β-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.
单苄基糖氨基酸（SAA）在醚环大小上有所不同（含有氧杂环丁烷、呋喃环和吡喃环），被合成并整合到环十肽短杆菌肽 S（GS）的一个β-转角区域中。CD、NMR 光谱、建模和 X 射线衍射表明，整合的 SAA 部分的环大小决定了它们顺式取向的羧基和氨甲基取代基的空间定位，从而微妙地影响与序列中相邻氨基酸的酰胺键。与 GS 本身不同，含 SAA 的肽的构象行为取决于溶剂。含吡喃环 SAA 的衍生物疏水性略低，溶血活性降低，但具有与 GS 相似的抗菌特性。
