Departament de Química, Universitat Autònoma de Barcelona, Bellaterra, 08193 Barcelona, Spain.
Amino Acids. 2011 Aug;41(3):673-86. doi: 10.1007/s00726-011-0912-4. Epub 2011 May 4.
Two diastereomeric series of hybrid γ,γ-peptides derived from conveniently protected derivatives of (1R,2S)- and (1S,2R)-3-amino-2,2-dimethylcyclobutane-1-carboxylic acid and cis-4-amino-L: -proline joined in alternation have efficiently been prepared through convergent synthesis. High-resolution NMR experiments show that these compounds present defined conformations in solution affording very compact structures as the result of intra and inter residue hydrogen-bonded ring formation. (R,S)-cyclobutane containing peptides adopt more twisted conformations than (S,R) diastereomers. In addition, all these γ-peptides have high tendency to aggregation providing vesicles of nanometric size, which were stable when allowed to stand for several days, as verified by transmission electron microscopy.
已通过汇聚合成高效制备了两种非对映异构系列的混合 γ,γ-肽，这些肽由（1R,2S）-和（1S,2R）-3-氨基-2,2-二甲基环丁烷-1-羧酸和顺式-4-氨基-L: -脯氨酸的方便保护衍生物交替连接而成。高分辨率 NMR 实验表明，这些化合物在溶液中呈现出确定的构象，由于形成了内和外残基氢键环，因此形成了非常紧凑的结构。（R,S）-环丁烷含肽比（S,R）非对映异构体具有更多的扭曲构象。此外，所有这些 γ-肽都具有强烈的聚集倾向，提供纳米级大小的囊泡，当允许静置数天时，通过透射电子显微镜证实这些囊泡是稳定的。
