An improved, scalable synthesis of bis-amino acids

作者：Cheong Jae Eun; Pfeiffer Conrad T; Northrup Justin D; Parker Matthew F L; Schafmeister Christian E^*

来源：Tetrahedron Letters, 2016, 57(44): 4882-4884.

DOI：10.1016/j.tetlet.2016.09.032

• Spiroligomer
• Bis-amino acids
• Amino acids
• Peptidomimetics
• Diastereomers

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.

• 出版日期2016-11-2