157662-41-4Relevant articles and documents
Allosteric modulation of the dopamine receptor by conformationally constrained type VI β-turn peptidomimetics of Pro-Leu-Gly-NH2
Vartak, Ashish P.,Skoblenick, Kevin,Thomas, Nancy,Mishra, Ram K.,Johnson, Rodney L.
, p. 6725 - 6729 (2008/09/17)
A peptidomimetic of Pro-Leu-Pro-NH2, 7, possessing an indolizidinone type VI β-turn mimic was synthesized via improved high-yielding protocols for the preparation and Cbz protection of α-allylproline. Bicyclic peptidomimetic 7 and spirobicylic
Constrained peptidomimetics for TRH: cis-peptide bond analogs
Tong, Yunsong,Olczak, Jacek,Zabrocki, Janusz,Gershengorn, Marvin C,Marshall, Garland R,Moeller, Kevin D
, p. 9791 - 9800 (2007/10/03)
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.
Novel bicyclic lactams as XaaPro type VI β turn mimics: Design, synthesis, and evaluation
Kim, Kyonghee,Dumas, Jean-Philippe,Germanas, Juris P.
, p. 3138 - 3144 (2007/10/03)
The design, enantioselective synthesis, and structural characterization of novel bicyclic lactams as peptide mimics of the type VI β turn is described. The mimics duplicate the conformation of the backbone and disposition of the side-chain atoms of the central two residues of the turn. The Gly L-Pro mimic, lactam 6, was prepared in good overall yield starting from (S)-2-(2'-propenyl)proline. 1H NMR spectroscopy defined the relative stereochemistry of the substituents and conformational characteristics of the six-membered ring of the lactam; X-ray crystallographic analysis confirmed the conformational and stereochemical assignment. Examination of the crystal structure of lactam 6 revealed that the central amide bond was twisted appreciably out of planarity. The twisting of the amide bond was attributed to angle strain resulting from the presence of the sp2-hybridized nitrogen atom at the junction of the two rings. Alkylation of the enolate of the N,N-dimethylformamidine derivative of lactam 6 with benzyl bromide afforded stereoselectively the formamidine 11, a mimic of an L-Phe L-Pro dipeptide in the type VI turn conformation. The efficient synthetic route to highly functionalized peptidomimetics such as 11 will prove highly useful in peptide structure-function studies.
DESIGN, SYNTHESIS AND EVALUATION OF A NOVEL BICYCLIC LACTAM AS A GLY-PRO TYPE VI BETA-TURN MIMIC
Dumas, Jean-Philippe,Germanas, Juris Paul
, p. 1493 - 1496 (2007/10/02)
The stereoselective synthesis and conformational evaluation of Gly-Pro type VI turn mimic 7, the first mimetic to constrain the central three bonds and incorporate the side chain groups of a beta-turn, is described.A superimposition of the crystallographi
