Olsen C A, Lambert M, Witt M, Franzyk H, Jaroszewski J W
Department of Medicinal Chemistry, Faculty of Pharmaceutical Sciences, University of Copenhagen, Copenhagen, Denmark.
Amino Acids. 2008 Apr;34(3):465-71. doi: 10.1007/s00726-007-0546-8. Epub 2007 May 23.
N-alkyl-beta-alanine oligomers (beta-peptoids) with alpha-chiral side chains [(R)- or (S)-1-(phenylethyl)amino groups] were synthesized and analyzed by CD spectroscopy. These chiral beta-peptoid homomers exhibited chain-length-dependent and solvent-dependent ellipticity, strongly indicating the presence of a secondary structure in solution. The CD behaviour was only slightly temperature-dependent upon heating, as also previously observed for stable alpha-peptoid helices containing the same type of side chains. Thus, the data presented here comprise the first evidence for a chain length-dependent secondary folding of compounds with this novel peptidomimetic backbone design. In addition, applicability of a novel hyphenated technique, HPLC-SPE-NMR/MS, for analysis of crude SPPS reaction products was demonstrated.
合成了带有α-手性侧链[（R）-或（S）-1-（苯乙基）氨基]的N-烷基-β-丙氨酸低聚物（β-类肽），并通过圆二色光谱法进行了分析。这些手性β-类肽均聚物表现出链长依赖性和溶剂依赖性椭圆率，强烈表明溶液中存在二级结构。正如之前在含有相同类型侧链的稳定α-类肽螺旋中所观察到的那样，圆二色行为在加热时仅略微依赖于温度。因此，此处呈现的数据首次证明了具有这种新型拟肽骨架设计的化合物存在链长依赖性二级折叠。此外，还展示了一种新型联用技术HPLC-SPE-NMR/MS用于分析固相肽合成反应粗产物的适用性。
