Catechol: A minimal scaffold for non-peptide peptidomimetics of the i + 1 and i + 2 positions of the beta-turn of somatostatin.
The design, synthesis, and evaluation of a series of catechol-based non-peptide peptidomimetics of the peptide hormone somatostatin have been achieved. These ligands comprise the simplest known non-peptide mimetics of the i + 1 and i + 2 positions of the somatostatin beta-turn. Incorporation of an additional side chain to include the i position of the beta-turn induces a selective 9-fold affinity enhancement at the sst2 receptor.
Mowery
Brendan P
BP
Department of Chemistry, University of Pennsylvania, Philadelphia, Pennsylvania 19104, USA.
Prasad
Vidya
V
Kenesky
Craig S
CS
Angeles
Angie R
AR
Taylor
Laurie L
LL
Feng
Jin-Jye
JJ
Chen
Wen-Long
WL
Lin
Atsui
A
Cheng
Fong-Chi
FC
Smith
Amos B
AB
Hirschmann
Ralph
R
D002396:Catechols / Q000737:chemistry*; D008958:Models, Molecular; D018716:Molecular Mimicry; D013004:Somatostatin / Q000737:chemistry*
D002396:Catechols; D013004:Somatostatin; C034221:catechol