5618 Journal of Medicinal Chemistry, 2009, Vol. 52, No. 18
Lukaszuk et al.
(24) Seebach, D.; Overhand, M.; Kuhnle, F. N. M.; Martinoni, B.;
Oberer, L.; Hommel, U.; Widmer, H. β-peptides: Synthesis by
Arndt-Eistert homologation with concomitant peptide coupling.
Structure determination by NMR and CD spectroscopy and by
X-ray crystallography. Helical secondary structure of a beta-
hexapeptide in solution and its stability towards pepsin. Helv.
Chim. Acta 1996, 79, 913–941.
(25) Seebach, D.; Gardiner, J. β-Peptidic peptidomimetics. Acc. Chem.
Res. 2008, 41, 1366–1375.
(26) Seebach, D.; Rueping, M.; Arvidsson, P. I.; Kimmerlin, T.;
Micuch, P.; Noti, C.; Langenegger, D.; Hoyer, D. Linear, Pepti-
dase-Resistant β2/β3-Di-and R/β3-Tetrapeptide Derivatives with
Nanomolar Affinities to a Human Somatostatin Receptor. Helv.
Chim. Acta 2001, 84, 3503–3510.
(27) Hook, D. F.; Gessier, F.; Noti, C.; Kast, P.; Seebach, D. Probing
the Proteolytic Stability of β-Peptides Containing R-Fluoro- and
R-Hydroxy-β-Amino Acids. ChemBioChem. 2004, 5, 691–706.
(28) Seebach, D.; Abele, S.; Schreiber, J. V.; Martinoni, B.; Nussbaum,
A. K.; Schild, H.; Schulz, H.; Hennecke, H.; Woessner, R.; Bitsch,
F. Biological and Pharmacokinetic Studies with β-Peptides. Chimia
1998, 52, 734–739.
(41) Pulka, K.; Feytens, D.; Van den Eynde, I.; De Wachter, R.;
Kosson, P.; Misicka, A.; Lipkowski, A.; Chung, N. N.; Schiller,
P. W.; Tourwe, D. Synthesis of 4-amino-3-oxo-tetrahydroazepino-
[3,4-b]indoles: new conformationally constrained Trp analogs.
Tetrahedron 2007, 63, 1459–1466.
(42) Kyle, D. J.; Martin, J. A.; Farmer, S. G.; Burch, R. M. Design and
conformational analysis of several highly potent bradykinin
receptor antagonists. J. Med. Chem. 1991, 34, 1230–1233.
(43) Schiller, P. W.; Weltrowska, G.; Berezowska, I.; Nguyen, T. M.;
Wilkes, B. C.; Lemieux, C.; Chung, N. N. The TIPP opioid peptide
family: development of delta antagonists, delta agonists, and mixed
mu agonist/delta antagonists. Biopolymers 1999, 51, 411–425.
(44) Casimir, J. R.; Iterbeke, K.; Van Den, N. W.; Trescol-Biemont, M.
C.; Dumortier, H.; Muller, S.; Gerlier, D.; Rabourdin-Combe, C.;
Tourwe, D.; Paris, J. Conformational restriction of the Tyr53 side-
chain in the decapeptide HE. J. Pept. Res. 2000, 56, 398–408.
(45) Ballet, S.; Frycia, A.; Piron, J.; Chung, N. N.; Schiller, P. W.;
Kosson, P.; Lipkowski, A. W.; Tourwe, D. Synthesis and biological
evaluation of constrained analogues of the opioid peptide H-Tyr-D-
Ala-Phe-Gly-NH2 using the 4-amino-2-benzazepin-3-one scaffold.
J. Pept. Res. 2005, 66, 222–230.
(29) Heck, T.; Limbach, M.; Geueke, B.; Zacharias, M.; Gardiner, J.;
Kohler, H.-P. E.; Seebach, D. Enzymatic Degradation of β- and
Mixed R,β-Oligopeptides. Chem. Biodiversity 2006, 3, 1325–
1348.
(30) Geueke, B.; Kohler, H. P. Bacterial beta-peptidyl aminopeptidases:
on the hydrolytic degradation of beta-peptides. Appl. Microbiol.
Biotechnol. 2007, 74, 1197–1204.
(31) Lelais, G.; Micuch, P.; Josien-Lefebvre, D.; Rossi, F.; Seebach, D.
Preparation of Protected β2- and β3-Homocysteine, β2- and β3-
Homohistidine and β2-Homoserine for Solid-Phase Syntheses.
Helv. Chim. Acta 2004, 87, 3131–3159.
(32) Cowell, S. M.; Lee, Y. S.; Cain, J. P.; Hruby, V. J. Exploring
Ramachandran and chi space: conformationally constrained ami-
no acids and peptides in the design of bioactive polypeptide ligands.
Curr. Med. Chem. 2004, 11, 2785–2798.
(33) Hruby, V. J.; Balse, P. M. Conformational and topographical
considerations in designing agonist peptidomimetics from peptide
leads. Curr. Med. Chem. 2000, 7, 945–970.
(34) Hruby, V. J. Design in topographical space of peptide and pepti-
domimetic ligands that affect behavior. A chemist’s glimpse at the
mind-body problem. Acc. Chem. Res. 2001, 34, 389–397.
(35) Gibson, S. E.; Guillo, N.; Tozer, M. J. Towards control of c-space:
Conformationally constrained analogues of Phe, Tyr, Trp and His.
Tetrahedron 1999, 55, 585–615.
(46) Hintermann, T.; Seebach, D. A useful modification of the Evans
auxiliary: 4-isopropyl-5,5-diphenyloxazolidin-2-one. Helv. Chim.
Acta 1998, 81, 2093–2126.
(47) Seebach, D.; Beck, A. K.; Capone, S.; Deniau, G.; Groselj, U.;
Zass, E. Enantioselective Preparation of β-Amino Acid Derivatives
for β-Peptide Synthesis. Synthesis 2009, 2009, 1–32.
(48) Demaegdt, H.; Vanderheyden, P.; De Backer, J. P.; Mosselmans,
S.; Laeremans, H.; Le, M. T.; Kersemans, V.; Michotte, Y.;
Vauquelin, G. Endogenous cystinyl aminopeptidase in Chinese
hamster ovary cells: characterization by [125I]Ang IV binding and
catalytic activity. Biochem. Pharmacol. 2004, 68, 885–892.
(49) Demaegdt, H.; Lenaerts, P. J.; Swales, J.; De Backer, J. P.; Laere-
mans, H.; Le, M. T.; Kersemans, K.; Vogel, L. K.; Michotte, Y.;
Vanderheyden, P.; Vauquelin, G. Angiotensin AT4 receptor ligand
interaction with cystinyl aminopeptidase and aminopeptidase N:
[
125I]angiotensin IV only binds to the cystinyl aminopeptidase apo-
enzyme. Eur. J. Pharmacol. 2006, 546, 19–27.
(50) Irons, D. W.; Davison, J. M.; Baylis, P. H. Evaluation of enzyme
inhibitors of cystinyl aminopeptidase and application to the mea-
surement of immunoreactive atrial natriuretic peptide in human
pregnancy. Clin. Chim. Acta 1994, 231, 185–191.
(51) Sardinia, M. F.; Hanesworth, J. M.; Krishnan, F.; Harding, J. W.
AT4 receptor structure-binding relationship: N-terminal-modified
angiotensin IV analogues. Peptides 1994, 15, 1399–1406.
(36) Tourwe, D.; Verschueren, K.; Frycia, A.; Davis, P.; Porreca, F.;
Hruby, V. J.; Toth, G.; Jaspers, H.; Verheyden, P.; Van, B. G.
Conformational restriction of Tyr and Phe side chains in opioid
peptides: information about preferred and bioactive side-chain
topology. Biopolymers 1996, 38, 1–12.
(52) Axen, A.; Andersson, H.; Lindeberg, G.; Ronnholm, H.; Kortesmaa,
J.; Demaegdt, H.; Vauquelin, G.; Karlen, A.; Hallberg, M. Small
potent ligands to the insulin-regulated aminopeptidase (IRAP)/
AT(4) receptor. J. Pept. Sci. 2007, 13, 434–444.
(53) Demaegdt, H.; Lukaszuk, A.; Buyser, E. D.; Backer, J.-P. D.;
ꢀ
Szemenyei, E.; Toth, G.; Chakravarthy, S.; Panicker, M.;
(37) Kazmierski, W.; Hruby, V. J. A new approach to receptor ligand
design: synthesis and conformation of a new class of potent and
highly selective [mu] opioid antagonists utilizing tetrahydroisoqui-
noline carboxylic acid. Tetrahedron 1988, 44, 697–710.
ꢀ
Michotte, Y.; Tourwe, D.; Vauquelin, G. Selective labelling of
IRAP by the tritiated AT4 receptor ligands [3H]Angiotensin IV
and its stable analog [3H]AL-11. 2009, submitted for publication .
(54) Olsen, J.; Cowell, G. M.; Konigshofer, E.; Danielsen, E. M.;
Moller, J.; Laustsen, L.; Hansen, O. C.; Welinder, K. G.; Engberg,
J.; Hunziker, W.; et al. Complete amino acid sequence of human
intestinal aminopeptidase N as deduced from cloned cDNA. FEBS
Lett. 1988, 238, 307–314.
ꢀ
ꢀ
(38) Sanchez-Sanchez, M. M.; Tel-Alberdi, L. M.; Rioseras, M. J.;
ꢀ
Rico-Ferreira, M. R.; Bermejo-Gonzalez, F. The Pictet-Spengler
Reaction on L-Histidine. Preparation of Conformationally
Restricted (þ)-Pilocarpine Analogs. Bull. Chem. Soc. Jpn. 1993,
66, 191–195.
(39) Kazmierski, W. M.; Yamamura, H. I.; Hruby, V. J. Topographic
Design of Peptide Neurotransmitters and Hormones on Stable
Backbone Templates;Relation of Conformation and Dynamics
to Bioactivity. J. Am. Chem. Soc. 1991, 113, 2275–2283.
(40) Ballet, S.; Mayorov, A. V.; Cai, M.; Tymecka, D.; Chandler, K. B.;
Palmer, E. S.; Rompaey, K. V.; Misicka, A.; Tourwe, D.; Hruby,
V. J. Novel selective human melanocortin-3 receptor ligands: use of
the 4-amino-1,2,4,5-tetrahydro-2-benzazepin-3-one (Aba) scaf-
fold. Bioorg. Med. Chem. Lett. 2007, 17, 2492–2498.
(55) Vanderheyden, P. M. L.; Fierens, F. L. P.; De Backer, J. P.;
Fraeyman, N.; Vauquelin, G. Distinction between surmountable
and insurmountable selective AT1 receptor antagonists by use of
CHO-K1 cells expressing human angiotensin II AT1 receptors.
Br. J. Pharmacol. 1999, 126, 1057–1065.
(56) Yung-Chi, C.; Prusoff, W. H. Relationship between the inhibition
constant (Ki) and the concentration of inhibitor which causes 50%
inhibition (I50) of an enzymatic reaction. Biochem. Pharmacol.
1973, 22, 3099–3108.