TY - JOUR
T1 - Synthesis of a Natural Product-Like Compound Collection through Oxidative Cleavage and Cyclization of Linear Peptides.
AU - Petersen, Rico
AU - Le Quement, Sebastian Thordal
AU - Nielsen, Thomas Eiland
PY - 2014
Y1 - 2014
N2 - Massive efforts in molecular library synthesis have
strived for the development of synthesis methodology which
systematically delivers natural product-like compounds of high
spatial complexity. Herein, we present a conceptually simple
approach that builds on the power of solid-phase peptide
synthesis to assemble precursor peptides (oligomers) designed
to undergo oxidative cascade reactions. By harnessing the
structural side-chain diversity and inherent stereochemical
features offered by readily available amino acids (monomers),
a proof-of-concept collection of 54 skeletally and stereochem-
ically diverse compounds was generated, and selected com-
pounds were elaborated into isoform-selective metalloprotease
inhibitors.
AB - Massive efforts in molecular library synthesis have
strived for the development of synthesis methodology which
systematically delivers natural product-like compounds of high
spatial complexity. Herein, we present a conceptually simple
approach that builds on the power of solid-phase peptide
synthesis to assemble precursor peptides (oligomers) designed
to undergo oxidative cascade reactions. By harnessing the
structural side-chain diversity and inherent stereochemical
features offered by readily available amino acids (monomers),
a proof-of-concept collection of 54 skeletally and stereochem-
ically diverse compounds was generated, and selected com-
pounds were elaborated into isoform-selective metalloprotease
inhibitors.
U2 - 10.1002/anie.201405747
DO - 10.1002/anie.201405747
M3 - Journal article
C2 - 25214457
SN - 0044-8249
VL - 126
SP - 1972
EP - 11976
JO - Angewandte Chemie
JF - Angewandte Chemie
ER -