posted on 2020-10-26, 18:13authored byChuan Dai, Fang Wang, Dandan Zhang, Lei Xu, Xuefeng Xia, Jinqiang Zhang
N-Aminoimidazolidin-2-one
(Aid)-containing peptides
with a constrained backbone present a novel class of peptidomimetics
for drug discovery. The introduction of Aid residues into peptide
sequences has been achieved by intramolecular Mitsunobu cyclization
of a serine side chain onto the α-NH of an aza-glycine residue.
The effectiveness of this new strategy was demonstrated by synthesizing
six Aid-containing analogues of angiotensin-(1–7) on solid
support. The Aid analogues of angiotensin-(1–7) exhibited increased
peptidase stability against human ACE and DPP3 and improved anti-inflammation
and antiproliferation activity.