Peptide Science — Present and Future: Proceedings of the 1st International Peptide Symposium

886 Pages·2002·35.351 MB·English

by  J.A. Wells, B. C. Cunningham, A. Braisted, S. Atwell, W. Delano, M. Ultsch (auth.), Yasutsugu Shimonishi (eds.)

PEPTIDE SCIENCE – PRESENT AND FUTURE
PEPTIDE SCIENCE –
PRESENT AND FUTURE
Proceedings of the 1st International
Peptide Symposium
Edited by
YASUTSUGU SHIMONISHI
Osaka University, Japan
KLUWER ACADEMIC PUBLISHERS
NEW YORK, BOSTON, (cid:39)(cid:50)(cid:53)(cid:39)(cid:53)(cid:40)(cid:38)(cid:43)(cid:55), (cid:47)(cid:3)(cid:50)(cid:49)(cid:39)(cid:50)(cid:49), MOSCOW
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Print ISBN 0-792-35271-8
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Contents
Preface xxxv
First International Peptide Symposium xxxvii
Acknowledgements xxxix
Abbreviations xli
Plenary lectures
1. From big molecules to smaller ones
J.A. Wells, B.C. Cunningham, A. Braisted, S. Atwell,
W. DeLano, M. Ultsch, M.A. Starovasnik and A.M. de Vos 1
2. Directions for solving the remaining problems in the synthesis
of large peptides
S. Sakakibara 6
General lectures
3. Peptide science: past, present and future
D. Brandenburg 15
4. Quo vadis? Where is peptide chemistry headed?
T. Shiba 21
Session A: Peptide mimetics and de novo design
5. Designing peptidomimetic antagonists for peptide receptors:
topochemical differences of agonists and antagonists
V.J. Hruby, S. Liao, G. Han, G. Bonner, M. Shenderovich,
J. Slaninova, F. Porreca, H.I. Yamamura and M.E. Hadley 26
6. Self-assembling homopolymeric peptide tapes in aqueous
solution
A. Aggeli, M. Bell, A. Strong, S. Radford and N. Boden 30
7. Peptides containing nonnatural amino acids with functional
side groups
M. Sisido 34
8. Active carbonates of N-protected amino alcohols for synthesis
of carbamate pseudopeptides
J.B. Halstrøm 39
v
vi Contents
9. Convenient one-pot synthesis of cystine-containing peptides
from protected peptidyl resins and its application to the
synthesis of bifunctional anti-HIV compounds
H. Tamamura, T. Ishihara, H. Oyake, A. Otaka and
N. Fujii 41
10. Stereoselective synthesis of two type (E)-alkene dipeptide
isosteres from a single substrate of β-aziridinyl-α,β-enoate
H. Tamamura, M. Yamashita, H. Muramatsu, T. Ibuka,
A. Otaka and N. Fujii 44
11. Design and synthesis of conformationally constrained
dipeptide containing the α-fluoroglycine residue
Y. Takeuchi, K. Kirihara, M. Kamezaki and N. Shibata 47
12. Screening of peptidomimetic tyrosine kinase inhibitors for
inducing programmed cell death
G. Kéri, L. Ôrfi, F. Hollósy, T. Vántus, J. Érchegyi, M. Idei,
A. Horváth, I. Teplán, A. Gazit, I. Peták, Z. Szegedi and
B. Szende 49
13. Molecular assembly of helix peptides vertically oriented on
gold surface
Y. Miura, S. Kimura, Y. Imanishi and J. Umemura 52
14. Gramicidin vesicles – self-assembly in water composed of
gramicidin A as hydrophobic core of membrane
D.-H. Kim, S. Kimura and Y. Imanishi 54
15. Design, synthesis, and characterization of a dimeric analog of
small globular protein (SGP) in solution and its biological and
channel-forming activities
T. Kiyota, E. Matsumoto, S. Yamashita, S. Lee and
G. Sugihara 57
16. Molecular design of cyclic peptides containing a non-natural
amino acid: novel synthetic approach to artificial ion channels
K. Donowaki, H. Ishida, Y. Inoue, Z. Qi, M. Sokabe,
M. Azumano and S. Futaki 59
17. Structure based design and characterization of exocyclic
peptidomimetics that inhibit TNFα binding to its receptor
W. Takasaki, Y. Kajino, K. Kajino, M.I. Greene and
R. Murali 61
18. A three-helix bundle metallopeptide destabilized at an acidic
condition
K. Suzuki and T. Tanaka 64
Contents vii
19. The alamethicin-leucine zipper hybrid peptide: modulation of
the assembling of transmembrane peptides through the
extramembrane peptide segments
S. Futaki, M. Fukuda and M. Niwa 67
20. BCvir: backbone cyclic peptide, which mimics the nuclear
localization signal of human immunodeficiency virus type 1
matrix protein, inhibits nuclear import and virus production in
non-dividing cells.
A. Friedler, N. Zakai, O. Karni, Y.C. Broder, L. Baraz,
M. Kotler, A. Loyter and C. Gilon 70
21. Self-assembling homopolymeric peptide tapes in moderately
polar organic solvents
A. Aggeli, M. Bell, R. Owens, A. Smith and N. Boden 73
22. Substrate specificities of artificial flavo-enzymes
K.-Y. Tomizaki, Y. Kakimoto, H. Akisada and N. Nishino 76
23. Catalytic activities of an artificial protein with designed loops
K.-Y. Tomizaki, D. Oka, Y. Kakimoto and N. Nishino 78
24. Catalytic activities of an artificial heme enzyme
K. Kaneko, K.-Y. Tomizaki and N. Nishino 80
25. A novel dioxopiperazine suitable as a β-turn constraint
J.S. Davies, M. Stelmach-Diddams, R. Fromentin,
A. Howells and R. Cotton 82
26. Amphiphilic β-structure formed by oligopeptides composed of
alternating hydrophilic and hydrophobic residues
S. Ono, K. Yamauchi, Y. Sugise, T. Tsutsumi, T. Okada,
T. Fujii and T. Yoshimura 85
27. Design of cyclic antimicrobial peptides with low hemolytic
activity
L.H. Kondejewski, M. Jelokhani-Niaraki, E.J. Prenner,
R.N.A.H. Lewis, R.N. McElhaney, R.E.W. Hancock and
R.S. Hodges 88
28. Synthesis and characterization of linear and cyclic
oligopeptides of 5-alkyl-substituted 3-aminobenzoic acids
K. Endo, H. Takahashi, T. Kurusu, K. Kaji and A. Sida 92
29. Theoretical analysis of βαβαβ-type packing motifs formed by
alternate intramolecular arrangements of three α-helices and
three β-strands
M. Oka and T. Hayashi 95
viii Contents
30. Theoretical analysis of β-type packing motifs formed by
intramolecular arrangements of β-strands
M. Oka and T. Hayashi 98
31. Theoretical analysis of αββα-type packing motifs formed by
intramolecular arrangements of two α-helices and two β-
strands
M. Oka and T. Hayashi 101
32. Self-catalytic conversion of peptides from α-helix to α-
structural amyloid
Y. Takahashi, A. Ueno and H. Mihara 104
33. Design, synthesis and characterization of heme-conjugated
two-α-helix peptides
S. Sakamoto, A. Ueno and H. Mihara 107
34. Self-assembly of heme-conjugated two-α-helix peptides
I. Obataya, S. Sakamoto, A. Ueno and H. Mihara 110
35. Construction of porphyrin-binding peptides mimicking anti-
heme monoclonal antibody
M. Takahashi, A. Ueno, T. Uda and H. Mihara 113
36. Construction of cyclodextrin–peptide conjugates and their
molecular sensing properties
S. Matsumura, S. Sakamoto, A. Ueno and H. Mihara 115
37. Interaction of bundled Ser-rich peptides with phospholipid
bilayer
K. Yoshida, N. Ohmori, T. Niidome, T. Hatakeyama and
H. Aoyagi 117
38. Topographically designed analogues of c[D-Pen², Pen5,
Nle6]deltorphin I with stereoisomers of β-MePhe or β-iPrPhe
in position 3
A. Misicka, J. Lin, K. Hosohata, H.I. Yamamura, P. Davis,
F. Porreca and V.J. Hruby 119
39. Engineering novel mini-proteins by the transfer of active sites
to small disulfide stabilized natural scaffolds
C. Vita, E. Drakopoulou, J. Vizzavona, P. Garnier and
A. Ménez 121
Session B: Peptide combinatorial libraries
40. Preparation of heterocyclic positional scanning combinatorial
libraries from peptides
R.A. Houghten, S.E. Blondelle, C. Dooley, J.-P. Meyer,
J.M. Ostresh and A. Nefzi 123
Contents ix
41. Design and synthesis of a lactam bridge stabilized coiled-coil
template for library display
M.E. Houston, R.T. Irvin and R.S. Hodges 128
42. Diversity of synthetic peptides
Y. Konishi, J.J. Slon-Usakiewicz and G. Pietrzynski 132
43. Manual construction of combinatorial resin bound tripeptide
library (one peptide on one bead) and screening to find
antioxidative peptides
T. Yasuhara and K. Nokihara 134
44. Selection of peptides that bind to α-lactalbumin from phage
display library
T. Nakamura, K. Hagiwara, K. Nitta and K. Takase 136
45. Identification of a novel analgesic peptide including an
unnatural amino acid from peptide libraries synthesized with a
multipeptide synthesizer
I. Maeda, N. Kanemoto, K. Ogino, M. Kuwahara, Y. Goto,
M. Adachi, T. Taki, M. Ohtani, Y. Muneoka, T. Kawakami
and S. Aimoto 139
46. Artificial proteins screened from combinatorial chemical
libraries with strong binding to double-stranded
oligodeoxyribonucleotides: towards repressors to long terminal
repeat controlled viral transcription.
S.R.K. Hoffmann and B. Gutte 141
47. Synthesis, conformational analysis and application of tropane-
based Fmoc-amino acid derivatives: novel antagonists of
fibrinogen receptor, GPIIb/IIIa
P.E. Thompson, D.L. Steer, K.A. Higgins, M.-I. Aguilar and
M.T.W. Hearn 144
Session C: Novel methodologies in structural analyses
48. Accurate peptide sequencing by mass spectrometry
T. Takao, W. Mo, J. Fernandez-de-Cossio, J. Gonzalez,
V. Besada, G. Padron and Y. Shimonishi 146
49. Characterization of sulfhydryl compounds attached to the
cysteinyl residue of proteins or peptides by on line post-
column derivatization
K. Nokihara and T. Yasuhara 152
50. Regioselective hydrolytic cleavage of N-terminal myristoyl-
peptide
K. Sugimoto, K. Okimura, N. Sakura and T. Hashimoto 154
x Contents
51. Selective removal of pyroglutamic acid residue from
biologically active pyroglutamyl-peptides by aqueous
methanesulfonic acid
J. Kobayashi, K. Ohki, N. Sakura and T. Hashimoto 157
52. Hydrolytic removal of acetyl-amino acid from acetyl-peptide
in methanesulfonic acid
K. Ohki, N. Sakura and T. Hashimoto 160
53. Determination of the binding-site structure of the atrial
natriuretic peptide receptor by stepwise-affinity alkylation
K.S. Misono 163
54. Structure of glycoside of Bombyx mori prothoracicotropic
hormone
S. Nagata, J. Kobayashi, H. Kataoka and A. Suzuki 166
55. Photophysics of sterically constrained phenylalanines
L. Lankiewicz, K. Stachowiak, A. Rzeska and W. Wiczk 168
56. Addressing combinatorial and peptide analysis by using
overpressured layer chromatography in comparison with high-
performance liquid chromatography and capillary
electrophoresis
G. Dibó, E. Mincsovics and Z. Majer 171
Session D: Peptides and proteins in signal transduction: Interaction with
membrane receptors and intracellular role
57. AVP(4-8)-induced branching signaling pathway was mediated
by a putative GPCR in rat brain
Q-W. Yan, L-Y. Qiao and Y-C. Du 174
58. The mechanisms of exocytosis induced by neurokinin peptides
in mast cells
H. Mukai, M. Kikuchi, Y. Suzuki and E. Munekata 179
59. Effects of dynorphins on free cytoplasmic calcium
concentration and insulin release in ob/ob mouse pancreatic β-
cells
S.V. Zaitsev, I.B. Efanova, A.M. Efanov and P-O. Berggren 183
60. The effect of magnesium ions on the uterotonic activity of
oxytocin analogs
J. Slaninová, L. Maletínská, M. ertová and Z. Procházka 185
61. Human thymopoietin beta-fragments: synthesis and antibody
studies
P.J.A. Weber, C.P. Eckard, S. Gonser, H. Otto, G. Folkers
and A.G. Beck-Sickinger 188
Contents xi
62. Cholecystokinin receptor parameters responsible for specific
cellular signalling
D. Gagne, N. Bernad, L. di Malta, R. Poosti,
J-C. Galleyrand, S. Poirot, D. Fourmy and J. Martinez 190
63. Sweetness-suppressing activities of gurmarin analogues missing
one disulfide bond
M. Ota, Y. Shimizu, K. Tonosaki and Y. Ariyoshi 193
64. Modeling of the somatostatin receptor (hsstr3)-ligand complex
J. Igarashi, X. Jiang and M. Goodman 195
65. Structural requirements of hyperalgesic nociceptin in receptor
binding and activation
T. Nose, R. Nakashima, R. Hatano, T. Sujaku, Y. Yamada,
A. Nagahisa and Y. Shimohigashi 198
66. Activation of phosphatidylinositol 3-kinase via epidermal
growth factor receptor in isolated rat hepatocytes
T. Fujioka and M. Ui 200
67. Agonist-antagonist structure-activity relationships of thrombin
receptor tethered ligand peptide
T. Fujita, T. Nose, M. Nakajima, Y. Inoue, N. Nakamura,
T. Inoue, T. Costa and Y. Shimohigashi 202
68. The first extracellular loop of the rat glucagon receptor
contains determinants of glucagon binding
C.G. Unson, A.M. Cypess, C-R. Wu, C.P. Cheung, B. Yoo
and R.B. Merrifield 205
69. A novel type of rat brain δ opioid receptors differenciated by
cyclopropylphenylalanine-containing enkephalin analog
Y. Chuman, T. Yasunaga, T. Costa and Y. Shimohigashi 207
70. Synthesis of dimeric novobiocins as chemical inducers of
dimerization for DNA gyrase-fused proteins
M. Miyazaki, J. Kim, K. Oshikiri, K. Saito and
S. Yokoyama 210
71. Computer biochemistry and molecular physiology of the
natural peptide ligands: different functional groups
A.A. Zamyatnin and O.L. Voronina 212
72. Bacterial peptide pheromone is imported where it directly
binds to an intracellular receptor
J. Nakayama, T. Horii and A. Suzuki 215