Synthesis of Fmoc- and Boc-Protected (2S,5S)- and (2R,5R)-5-Aminomethylprolines

Synthesis of Fmoc- and Boc-Protected (2S,5S)- and (2R,5R)-5-Aminomethylprolines: A. L. Bartuschat, N. Hegmann, M. R. Heinrich
Synthesis 2019, DOI: 10.1055/s-0037-1610304

Proline plays a peculiar role in peptides and proteins as it can induce a turn in the secondary structure, especially when flanked by a highly flexible glycine residue. Proline is in fact unable to function as H-bond donor and its peptide bonds have a more populated cis-geometry than other proteinogenic amino acids. Proline analogues have thus become important scaffolds for inducing specific geometries – and therefore functions – in peptides and proteins. A recent contribution from the group of Professor Markus R. Heinrich from the Friedrich- Alexander-Universität Erlangen-Nürnberg (Germany) described a new synthetic approach to stereodefined 5-aminomethylprolines.

The authors said: “Proline derivatives which enable a pH-dependent conformational fixation of the N-prolyl–CO bond in peptides offer new possibilities in ligand design and many other fields of medicinal chemistry.”
Get Trial Access to the chemistry journals
Download SYNFORM or read it online