Premium
An ‘Umpolung’ Route to Peptide Mimetics of Thyrotropin‐Releasing Hormone based on a cyclohexane framework
Author(s) -
Bös Michael,
Olson Gary L.,
Vincent George P.
Publication year - 1994
Publication title -
helvetica chimica acta
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.74
H-Index - 82
eISSN - 1522-2675
pISSN - 0018-019X
DOI - 10.1002/hlca.19940770207
Subject(s) - chemistry , umpolung , peptide , thyrotropin releasing hormone , cyclohexane , reagent , cyclohexenone , wittig reaction , side chain , combinatorial chemistry , stereochemistry , hormone , organic chemistry , biochemistry , nucleophile , catalysis , polymer
Peptide mimetics of thyrotropin‐releasing hormone (TRH) in which the peptide backbone is replaced by cyclohexane were synthesized from the cyclohexenone precursor 7 . The aromatic side chains of the mimetics were derived from the corresponding aldehydes which were attached to the cyclohexenone via the Wittig reagent 8 . The TRH mimetics are active in a mouse model of cognitive performance.