218
A. Caporale et al.
Kronenberg H, Abou-Samra A, Bringhurst F, Gardella T, Ju¨ppner H,
Segre G (1997) In: Thakker R (ed) Genetics of endocrine and
metabolic disorders. Chapman & Hall, London, pp 389–420
Kubasik M, Blom A (2005) Acceleration of short helical peptide
conformational dynamics by trifluoroethanol in an organic
solvent. ChemBioChem 6:1187–1190
with enhanced potency in activating the type-1 parathyroid
hormone receptor. J Biol Chem 275:21836–21843
Shimizu M, Carter PH, Khatri A, Potts JT, Gardella TJ (2001a)
Enhanced activity in parathyroid hormone-(1–14) and -(1–11):
novel peptides for probing ligand–receptor interactions. Endo-
crinology 142:3068–3074
Locardi E, Mammi S, Peggion E, Monaco V, Formaggio F, Crisma
M, Toniolo C, Bodo B, Rebuffat S, Kamphuis J, Broxterman Q
(1998) Conformation and membrane activity of an analogue of
the peptaibol antibiotic trichogin GA IV with a lipophilic amino
acid at the N terminus. J Pept Sci 4(6):389–399
Shimizu N, Guo J, Gardella TJ (2001b) Parathyroid hormone (1–14)
and (1–11) analogs conformationally constrained by a-amino-
isobutyric acid mediate full agonist responses via the juxta-
membrane region of the PTH
276:49003–49012
1 receptor. J Biol Chem
¨
Maity P, Konig B (2008) Enantio- and diastereoselective syntheses of
Shimizu N, Shimizu M, Tsang JC, Petroni BD, Khatri A, Potts JT,
Gardella TJ (2002) Residue 19 of the parathyroid hormone
(PTH) modulates ligand interaction with the juxtamembrane
region of the PTH-1 receptor. Biochemistry 41:13224–13233
Shimizu M, Dean T, Khatri A, Gardella TJ (2004) Amino-terminal
parathyroid hormone fragment analogs containing a, a-di-alkyl
amino acids at positions 1 and 3. J Bone Miner Res 19:2078–
2086
Shimizu N, Dean T, Tsang JC, Khatri A, Potts JT, Gardella TJ (2005)
Novel parathyroid hormone (PTH) antagonists that bind to the
juxtamembrane portion of the PTH/PTH-related protein recep-
tor. J Biol Chem 280:1797–1807
cyclic Ca-tetrasubstituted a-amino acids and their use to induce
stable conformations in short peptides. Biopolymers (Pept Sci)
90:8–27
Monticelli L, Mammi S, Mierke DF (2002) Molecular characteriza-
tion of a ligand-tethered parathyroid hormone receptor. Biophys
Chem 95:165–172
Moretto A, Formaggio F, Kaptein B, Broxterman QB, Wu L,
Keiderling TA, Toniolo C (2008) First homo-peptides undergo-
ing a reversible 310-helix/a-helix transition: critical main-chain
length. Biopolymers (Pept Sci) 90:567–574
Obrecht D, Bohdal U, Broger C, Bur D, Lehmann C, Ruffieux R,
¨
¨
Schonholzer P, Spiegler C, Muller K (1995) L-Phenylalanine
cyclohexylamide: a simple and convenient auxiliary for the
synthesis of optically pure a,a-disubstituted (R)- and (S)-amino
acids. Helv Chim Acta 78:563–580
Toniolo C (1989) Structure of conformationally constrained peptides:
from model compounds to bioactive peptides. Biopolymers
28:247–257
Toniolo C, Polese A, Formaggio F, Crisma M, Kamphuis J (1996)
Circular dichroism spectrum of a peptide 310-helix. J Am Chem
Soc 118:2744–2745
Toniolo C, Crisma M, Formaggio F, Peggion C (2001) Control of
peptide conformation by the Thorpe–Ingold effect (Ca-tetrasub-
stitution). Biopolymers (Pept Sci) 60:396–419
Toniolo C, Formaggio F, Tognon S, Broxterman QB, Kaptein B,
Huang R, Setnicka V, Keiderling TA, McColl IH, Hecht L,
Barron LD (2004) The complete chirospectroscopic signature
of the peptide 310-helix in aqueous solution. Biopolymers
75:32–45
Perczel A, Hollosi M, Foxman B, Fasman GD (1991) Conformational
analysis of pseudocyclic hexapeptides based on quantitative circular
dichroism(CD), NOE, and X-ray data. The pure CDspectra of type I
and type II beta-turns. J Am Chem Soc 113:9772–9784
Pines M, Adams AE, Stueckle S, Bessalle R, Rashti-Behar V, Chorev
M, Rosenblatt M, Suva LJ (1994) Generation and characteriza-
tion of human kidney cell lines stably expressing recombinant
human PTH/PTHrP. Endocrinology 135:1713–1716
Pioszak AA, Parker NR, Gardella TJ, Xu HE (2009) Structural basis
for parathyroid hormone-related protein binding to the parathy-
roid hormone receptor and design of conformation-selective
peptides. J Biol Chem 24:28382–28391
Polese A, Formaggio F, Crisma M, Valle G, Toniolo C, Bonora GM,
Broxterman QB, Kamphuis J (1996) Peptide helices as rigid
molecular rulers: a conformational study of isotactic homopep-
tides from a-methyl-a-isopropylglycine, [L-(aMe)Val]n. Chem
Eur J 2:1104–1111
Potts JT, Gardella TJ (2008) Progress, paradox, and potential:
parathyroid hormone research over five decades. Ann NY Acad
Sci 1117:196–208
Rance M, Sørensen OW, Bodenhausen G, Wagner G, Ernst RR,
Wu¨thrich K (1983) Improved spectral resolution in COSY 1H
NMR spectra of proteins via double quantum filtering. Biochem
Biophys Res Commun 117:479–485
Rosenblatt M, Goltzmann D, Keutmann HT, Tregear GW, Potts JT
(1976) Chemical and biological properties of synthetic, sulfur-free
analogues of parathyroid hormone. J Biol Chem 251:159–164
Santini A, Barone V, Bavoso A, Benedetti E, Di Blasio E, Fraternali
F, Lelj F, Pavone V, Pedone C, Crisma M, Bonora GM, Toniolo
C (1988) Structural versatility of peptides from Ca, a-dialkylated
glycines: a conformational energy calculation and X-ray dif-
fraction study of homopeptides from 1-aminocyclopentane-1-
carboxylic acid. Int J Biol Macromol 10:292–299
Scian M, Marin M, Bellanda M, Tou L, Alexander JM, Rosenblatt M,
Chorev M, Peggion E, Mammi S (2006) Backbone dynamics of
human parathyroid hormone (1–34): flexibility of the central region
under different environmental conditions. Biopolymers 84:147–160
Shimizu M, Potts JT, Gardella TJ (2000) Minimization of parathyroid
hormone. Novel amino-terminal parathyroid hormone fragments
´
Torras J, Zanuy D, Crisma M, Toniolo C, Betran O, Aleman C (2008)
Correlation between symmetry breaker position and the prefer-
ences of conformationally constrained homopeptides: a molec-
ular dynamics investigation. Biopolymer (Pept Sci) 90:695–706
Tsomaia N, Pellegrini M, Hyde K, Gardella TJ, Mierke DF (2004)
Toward parathyroid hormone minimization: conformational stud-
ies of cyclic PTH (1–14) analogues. Biochemistry 43:690–699
Vilardaga JP, Romero G, Friedman PA, Gardella JT (2011) Molecular
basis of parathyroid hormone receptor signalling and trafficking:
a family B GPCR paradigm. Cell Mol Life Sci. doi:10.1007/
Wenschuh H, Beyermann M, Krause E, Brudel M, Winter R,
Schu¨mann M, Carpino LA, Bienert M (1994) Fmoc amino acid
fluoride: convenient reagents for the solid-phase assembly of
peptides incorporating sterically hindered residues. J Org Chem
59:3275–3280
Willisch H, Hiller W, Hemmasi B, Bayer E (1991) Synthesis,
properties and crystal structure of the tripeptide boc-L-prolyl-L-
propargylglycyl-glycine methylester. Tetrahedron 47:3947–3958
Wittelsberger A, Corich M, Thomas BE, Lee BK, Barazza A,
Czodrowski P, Mierke DF, Chorev M, Rosenblatt M (2006) The
mid region of parathyroid hormone (1–34) serves as functional
docking domain in receptor activation. Biochemistry 45:
2027–2034
Wu¨thrich K (1986) NMR of proteins and nucleic acids. Wiley,
Weinheim
Yang JT, Wu CS, Martinez HM (1986) Calculation of protein
conformation from circular dichroism. Methods Enzymol
130:208–269
123