30189-36-7Relevant articles and documents
Heparin versus DNA: Chiral preferences in polyanion binding to self-assembled multivalent (SAMul) nanostructures
Bromfield, Stephen M.,Smith, David K.
, p. 10056 - 10059 (2015)
This communication presents simple cationic self-assembling multivalent (SAMul) first generation dendrons based on l or d lysine, which form identical nanoscale assemblies in terms of dimensions and charge densities but toward which DNA and heparin exhibit different chiral binding preferences. However, higher generation dendrons with larger hydrophilic head groups are bound identically by these polyanions, irrespective of chirality. We propose that well-organized chiral ligands on the surface of self-assembled nanostructures can exhibit enantioselective polyanion binding. This demonstrates that small structural changes can be amplified by self-assembly and impact on nanoscale binding.
A Collaborative Assembly Strategy for Tumor-Targeted siRNA Delivery
Sun, Qiong,Kang, Zisheng,Xue, Lingjing,Shang, Yunkai,Su, Zhigui,Sun, Hongbin,Ping, Qineng,Mo, Ran,Zhang, Can
, p. 6000 - 6010 (2015)
A novel "collaborative assembly" approach was reported for the synthesis of an siRNA delivery system via a combination of an electrostatically driven physical assembly and a facile click reaction-mediated chemical assembly, which showed various advantages
Ynamide-Mediated Thiopeptide Synthesis
Yang, Jinhua,Wang, Changliu,Xu, Silin,Zhao, Junfeng
supporting information, p. 1382 - 1386 (2019/01/08)
Exploration of the full potential of thioamide substitution as a tool in the chemical biology of peptides and proteins has been hampered by insufficient synthetic strategies for the site-specific introduction of a thioamide bond into a peptide backbone. A novel ynamide-mediated two-step strategy for thiopeptide bond formation with readily available monothiocarboxylic acids as thioacyl donors is described. The α-thioacyloxyenamide intermediates formed from the ynamides and monothiocarboxylic acids can be purified, characterized, and stored. The balance between their activity and stability enables them to act as effective thioacylating reagents to afford thiopeptide bonds under mild reaction conditions. Amino acid functional groups such as OH, CONH2, and indole NH groups need not be protected during thiopeptide synthesis. The modular nature of this strategy enables the site-specific incorporation of a thioamide bond into peptide backbones in both solution and the solid phase.
One-pot orthogonal copper-catalyzed synthesis and self-assembly of l-lysine-decorated polymeric dendrimers
Lu, Derong,Hossain, Md. D.,Jia, Zhongfan,Monteiro, Michael J.
, p. 1688 - 1702 (2015/03/31)
Synthetic peptides, including cyclic peptides and peptidomimetics, provide stability, protection, and long circulation times compared to free-circulating peptides. Dendritic structures with amino acids or peptides attached to the peripheral layer represent one form of peptidomimetics (i.e., a hybrid peptide/dendrimer construct) that has found use in biological applications. Constructing such dendritic structures from linear polymeric building blocks provides a further advantage of generating a highly ordered and defined structure in the nanoparticle size range. However, the rapid synthesis of such well-defined structures is still a challenge. In this work, we demonstrate that through modulating the copper activity concomitantly of the nitroxide radical coupling (NRC) and the azide-alkyne cycloaddition (CuAAC) reactions, polymeric dendrimers decorated with l-lysine on the periphery could be made rapidly in one pot at 25 °C. Three polymeric dendrimers were constructed with high purity (>94%) and with varying l-lysine density coated on the peripheral generation layer. The self-assembly of these dendrimers in water gave similar sizes to that found in organic solvents, suggesting that the aggregation number of dendritic structures in water was very low and possibly consisting of unimolecular micelles. The findings support the conclusion that the self-assembly of a dendritic architecture in water produces nanoparticles with predictable and well-controlled sizes. This synthetic methodology and the self-assembly properties represent an important step toward synthesizing peptide-decorated dendrimers targeted toward therapeutic applications.
