526222-97-9Relevant academic research and scientific papers
An improved, scalable synthesis of bis-amino acids
Cheong, Jae Eun,Pfeiffer, Conrad T.,Northrup, Justin D.,Parker, Matthew F.L.,Schafmeister, Christian E.
, p. 4882 - 4884 (2016/10/24)
trans-4-Hydroxy-L-proline derived bis-amino acids are chiral, cyclic building blocks that display two alpha-amino acids that are differentiated from each other with protecting groups. They are assembled into spiroligomers—rigid, shape-programmable spirocyclic oligomers that are both stereochemically and functionally diverse. The synthesis presented here focuses on recent improvements that allow for a convenient, large-scale synthesis of twelve stereochemically pure bis-amino acids from inexpensive trans-4-hydroxy-L-proline. The bis-amino acids differ in stereochemistry as well as the amine protecting group, one of which (para-nitrobenzyl carbamate) has not been previously incorporated into bis-amino acids.
The synthesis of functionalized nanoscale molecular rods of defined length
Levins, Christopher G.,Schafmeister, Christian E.
, p. 4702 - 4703 (2007/10/03)
We report a synthetic approach to spiro-ladder oligomers of defined length and structure that form water-soluble molecular rods. We describe the synthesis of a chiral molecular building block 1 and its assembly on solid support to form flexible chains that were then rigidified by the parallel formation of several diketopiperazine rings. Two molecular rods approximately 15 and 25 A in length were synthesized containing three and five monomers, respectively. The molecular rods were easily functionalized on both ends and were shown to have high water solubility, making them compatible with biological buffers. These molecules may find use as scaffolds for the display of ligands in chemical-biology applications and as spacers and construction materials for nanoscience applications. Copyright
