Spiroligomer

Spiroligomer scaffolds
Spiroligomer Scaffolds - (A) bis-amino acids (B) 3D Mock up of a bis-amino acids (C) Spiroligomer Trimer (D) 3D Mock up of a Spiroligomer

Spiroligomer molecules (also known as bis-peptides) are synthetic oligomers made by coupling pairs of bis-amino acids into a fused ring system.[1] Spiroligomer molecules are rich in stereochemistry and functionality because of the variety of bis-amino acids that are capable of being incorporated during synthesis.[2] Due to the rigidity of the fused ring system,[3] the three-dimensional shape of a Spiroligomer molecule – as well as the display of any functional groups – can be predicted, allowing for molecular modeling and dynamics.

  1. ^ Christian E. Schafmeister, Zachary Z. Brown, and Sharad Gupta "Shape-Programmable Macromolecules" Accounts of Chemical Research, (2008), 41(10), 1387-1398 doi:10.1021/ar700283y
  2. ^ Zachary Z. Brown and Christian E. Schafmeister, "Synthesis of Hexa- and Pentasubstituted Diketopiperazines from Sterically Hindered Amino Acids" Organic Letters, (2010), 12(7), 1436-1439 doi:10.1021/ol100048g
  3. ^ Gregory H. Bird, Soraya Pornsuwan, Sunil Saxena, and Christian E. Schafmeister, "Distance Distributions of End-Labeled Curved Bispeptide Oligomers by Electron Spin Resonance" ACSNano (2008), 2(9), 1857-1864 doi:10.1021/nn800327g