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芴甲氧羰基-苯丙氨酰-苯丙氨酸(Fmoc-FF)的不同N-端封端类似物

Differently N-Capped Analogues of Fmoc-FF.

作者信息

Diaferia Carlo, Rosa Elisabetta, Gallo Enrico, Morelli Giancarlo, Accardo Antonella

机构信息

Department of Pharmacy and CIRPeB, Research Centre on Bioactive Peptides "Carlo Pedone", University of Naples "Federico II", Via Montesano 49, 80131, Naples, Italy.

IRCCS Synlab SND, Via E., Gianturco 113, 80143, Naples, Italy.

出版信息

Chemistry. 2023 May 16;29(28):e202300661. doi: 10.1002/chem.202300661. Epub 2023 Apr 5.

Abstract

Short and ultra-short peptides have been recently envisioned as excellent building blocks for the formulation of hydrogels with appealing properties. Due to its simplicity and capability to gel under physiological conditions, Fmoc-FF (N -fluorenylmethoxycarbonyl-diphenylalanine), remains one of the most studied low molecular-weight hydrogelators. Since its first identification in 2006, a plethora of its analogues were synthetized and investigated for the fabrication of novel supramolecular materials. Here we report a description of the Fmoc-FF analogues in which the aromatic Fmoc group is replaced with other substituents. These analogues are distinguished into five different classes including derivatives: i) customized with solid phase peptide synthesis protecting groups; ii) containing non-aromatic groups, iii) containing aromatic groups, iv) derivatized with metal complexes and v) containing stimuli-responsive groups. The morphological, mechanical, and functional effects caused by this modification on the resulting material are also pointed out.

摘要

短肽和超短肽最近被视为用于制备具有吸引人特性的水凝胶的优良构建基元。由于其简单性以及在生理条件下形成凝胶的能力,芴甲氧羰基-苯丙氨酸二肽(Fmoc-FF,N-芴甲氧羰基-二苯基丙氨酸)仍然是研究最多的低分子量水凝胶剂之一。自2006年首次被鉴定以来,人们合成了大量其类似物,并对其用于制造新型超分子材料进行了研究。在此,我们报道了对Fmoc-FF类似物的描述,其中芳香族Fmoc基团被其他取代基取代。这些类似物可分为五类不同的衍生物:i)用固相肽合成保护基团定制的;ii)含有非芳香族基团的;iii)含有芳香族基团的;iv)用金属配合物衍生化的;v)含有刺激响应基团的。还指出了这种修饰对所得材料造成的形态、力学和功能影响。

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