TY - JOUR
T1 - Constrained peptidomimetics for TRH
T2 - cis-peptide bond analogs
AU - Tong, Yunsong
AU - Olczak, Jacek
AU - Zabrocki, Janusz
AU - Gershengorn, Marvin C.
AU - Marshall, Garland R.
AU - Moeller, Kevin D.
N1 - Funding Information:
We thank the National Institutes of Health (RO1 GM5324001 and R01 DK43036) for their generous financial support. In addition, we thank the Washington University High Resolution NMR Facility, partially supported by NIH grants RR02004, RR05018, and RR07155, and the Washington University Mass Spectrometry Resource Center, partially supported by NIH RR00954, for their assistance.
PY - 2000/12/8
Y1 - 2000/12/8
N2 - Two constrained analogs of the tripeptide hormone thyroliberin (TRH) have been synthesized. In both, the HisPro peptide bond of the hormone has been 'locked' into a cis-conformation. In the first analog, the constraint used was identical to the constraint used in an earlier trans-peptide bond analog that was a potent agonist for the TRH endocrine receptor TRH-R1. The second analog was built in order to take advantage of a tetrazole ring as the cis-peptide bond constraint. Neither analog showed agonist or antagonist behavior toward TRH-R1 suggesting that the cis-peptide bond conformation may not play a role in the affinity of TRH for TRH-R1. (C) 2000 Elsevier Science Ltd.
AB - Two constrained analogs of the tripeptide hormone thyroliberin (TRH) have been synthesized. In both, the HisPro peptide bond of the hormone has been 'locked' into a cis-conformation. In the first analog, the constraint used was identical to the constraint used in an earlier trans-peptide bond analog that was a potent agonist for the TRH endocrine receptor TRH-R1. The second analog was built in order to take advantage of a tetrazole ring as the cis-peptide bond constraint. Neither analog showed agonist or antagonist behavior toward TRH-R1 suggesting that the cis-peptide bond conformation may not play a role in the affinity of TRH for TRH-R1. (C) 2000 Elsevier Science Ltd.
KW - TRH endocrine receptor
KW - Tetrazole ring
KW - Tripeptide hormone thyroliberin
UR - http://www.scopus.com/inward/record.url?scp=0034624207&partnerID=8YFLogxK
U2 - 10.1016/S0040-4020(00)00886-3
DO - 10.1016/S0040-4020(00)00886-3
M3 - Article
AN - SCOPUS:0034624207
SN - 0040-4020
VL - 56
SP - 9791
EP - 9800
JO - Tetrahedron
JF - Tetrahedron
IS - 50
ER -