OLID PHASE SYNTHESIS - GBV · Innovation and Perspectives in OLID PHASE SYNTHESIS & COMBINATORIAL...
Transcript of OLID PHASE SYNTHESIS - GBV · Innovation and Perspectives in OLID PHASE SYNTHESIS & COMBINATORIAL...
Innovation and Perspectives in
OLID PHASESYNTHESIS& COMBINATORIAL LIBRARIES
Peptides, Proteins and Nucleic AcidsSmall Molecule Organic Chemical Diversity
1996Editor: Roger Epton
Collected PapersFourth International Symposium12th -16th September, 1995Edinburgh, Scotland, UK
Mayflower Scientific Limited, Birmingham, 1996
TABLE OF CONTENTS
Preface v
Acknowledgements vi
SYNTHESIS / STRATEGY OF SYNTHESIS
1. METHODOLOGY FOR CHEMICAL SYNTHESIS OF PROTEINS 1R. Ramage, G.W. Biggin, A.R. Brown, A. Comer, A. Davison, L. Draffan,Lu Jiang, G. Morton, N. Robertson, K.T. Shaw, G. Tennant, K. Urquhartand J. Wilken
2. SOLID PHASE SYNTHESIS OF OLIGORIBONUCLEOTIDES CONTAININGSITE-SPECIFIC MODIFICATIONS 11
Sabine Schmidt, Richard L. Grenfell, Jan Fogg, Terry V. Smith, Jane A. Grasby,Karin Mersmann and Michael J. Gait.
3. THE SYNTHESIS, AND SEPARATION OF PEPTIDES, DNA AND HYBRIDMOLECULES 19
Ronald M. Cook and Derek Hudson
Advances in Solid Phase Peptide/Protein Synthesis (I)
4. CHEMICAL SYNTHESIS OF PROTEINS: A PRACTICAL SOLID-PHASESEGMENT ASSEMBLY APPROACH 27
Tony Johnson, Leonard C. Packman and Martin Quibell
5. AN EFFICIENT AND RELIABLE SOLID PHASE SEGMENT ASSEMBLYAPPROACH FOR SMALL PROTEIN SYNTHESIS THROUGH THE USE OFBACKBONE AMIDE-PROTECTED PEPTIDE SEGMENTS 37
Martin Quibell, Leonard C. Packman and Tony Johnson
6. ADVANCES IN THE USE OF ONIUM-BASED COUPLING REAGENTS:APPLICATION FOR SOLID-PHASE PEPTIDE SYNTHESIS ANDCOMBINATORIAL LIBRARIES 41
Steven A. Kates, Salvatore A. Triolo, G. William Griffin, Lee W. Herman,George Tarr, Nura A. Sole, Elke Diekmann, Ayman El-Faham,Dumitru Ionescu, Fernando Albericio and Louis A. Carpino
Advances in Solid Phase Oligonucleotide DNA, RNA, PNA etc. Synthesis (I)
i. SYNTHESIS OF PNA ON A PEPTIDE SYNTHESIZER: SOLID PHASE-PNAAFFINITY PROBES FOR SEQUENCE SPECIFIC ISOLATION FROM TOTALDNA !":.:.. 51
Ken Otteson, Dave Knorr and Alex Andrus
8. SYNTHESIS AND APPLICATIONS OF SPATIALLY ADDRESSABLEOLIGONUCLEOTIDE ARRAYS 57
Stephen C. Case-Green, Kalim U. Mir, Natalie Milner and Edwin M. Southern
9. SYNTHESIS OF POLY AMIDE NUCLEIC ACIDS USING A NEWPROTECTION SCHEME WHICH IS FULLY COMPATIBLE WITHOLIGONUCLEOTIDE SYNTHESIS 61
G. Breipohl, D.W. Will, D. Langer, J. Knolle and E. Uhlmann
10. SOLID-PHASE SYNTHESIS OF PNA-DNA CHIMERIC OLIGOMERS 65D.W. Will, G. Breipohl, D. Langner and E. Uhlmann
11. PHYSICOCHEMICAL PROPERTIES OF 1,5-ANHYDRO-HEXITOL
NUCLEIC ACIDS 69
Arthur Van Aerschot, Chris Hendrix, Use Verheggen and Piet Herdewijn.
SYNTHESIS / AUTOMATED SYNTHESIS / APPLICATIONS
Automated Solid Phase Synthesis
12. AUTOMATED PEPTIDE SYNTHESIS UTILIZING URETHANE-PROTECTEDN-CARBOXYANHYDRIDES (UNCA'S) 73
Murray Goodman, Susan H. H. Wang, Jaimie K. Rueter, Joseph P. Taulane andJacqueline McCandless
13. SYNTHESIS OPTIMISATION USING ON-LINE MONITORING IN A NEWCONTINUOUS FLOW SYNTHESIZER 87
H. Gausepohl, C. Behn, R. Schopfer and R. W. Frank
14. MARS - MULTIPLE AUTOMATIC ROBOT SYNTHESIZER FEATURING ANOVEL TIMING PROCEDURE AND RANDOM ACCESS TO REAGENTS ANDREACTION VESSELS 93
Viktor Krchnak and Michal Lebl
15. MINIATURIZATION IN CHEMISTRY: CHEMICAL POSSIBILITIES ANDPHYSICOCHEMICAL PROPERTIES OF POLYMERIC MICROREACTORS 97
W. Rapp, G. Nicholson, M. Maier, G. Schlotterbeck, M. Purschand K. Albert
Small Molecule Organic Chemical Libraries (I & II)
16. SYNTHESIS OF BINARY ENCODED SMALL MOLECULE LIBRARIES ANDTHEIR APPLICATION TO DRUG DISCOVERY AND OPTIMIZATION 101
John C. Chabala, John J. Baldwin, Jonathan J. Burbaum, Daniel Chelsky,Lawrence W.Dillard, Ian Henderson, Ge Li, Michael H. J. Ohlmeyer,Troy L. Randle, John C. Reader, Laura Rokosz and Nolan H. Sigal
17. THE USE OF POLYMER-ASSISTED ORGANIC SYNTHESIS FOR THEPRODUCTION OF SMALL ORGANIC MOLECULES 107
Irving Sucholeiki
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18. SOLID PHASE POLYAMINE LINKERS - SYNTHESIS AND COMBINATORIALUTILITY I l l
Ian Marsh, Helen Smith, Catherine Leblanc and Mark Bradley
19. SYNTHESIS OF QUINOLINE ANTIBIOTICS BY DIVERSOMER™TECHNOLOGY 115
Alasdair A. MacDonald, Sheila Hobbs De Witt, Eleonora Hoganand Robert Ramage
Advances in Solid Phase Peptide / Protein Synthesis (II)
20. USE OF THE ALLYLIC HYCRON ANCHOR IN SOLID PHASE PEPTIDESYNTHESIS 117
Markus Gewehr, Horst Kunz, Arnulf Lauterbach, Birgit Lohr and Oliver Seitz
21. N-PROTECTED AMINOACYLOXOCROTONATES - VERSATILE NEWTOOLS IN PEPTIDE SYNTHESIS COMBINING BOTH SOLUTIONAND SOLID PHASE HYCRAM® ADVANTAGES 121
Christian Birr, Giinther Braum and Axel Lifferth
22. PREPARATION OF Ca-METHYL AMINO-ACIDS AND THEIR USE INSOLID PHASE SYNTHESIS 125
M. Ayoub, A. Brunissen, G. Chassaing, S. Lavielle and A. Loffet
23. AMINO ACID FLUORIDES IN PEPTIDE SYNTHESIS - EFFICIENT ACYLATIONOF HYDROXYL FUNCTIONS AND EXTENSION OF THE METHOD TO VERYBULKY AMINO ACID RESIDUES 131
Holger Wenschuh, Michael Beyermann, Dorthe Granitza, Hanka Haber,George A. Truran, Michael Bienert and Louis A. Carpino
Advances in Nucleic Acid Synthesis (II)
24. OPTIMIZED AUTOMATED SOLID PHASE SYNTHESIS OFOLIGONUCLEOTIDES AND DERIVATIVES 135
G. Alvarado Urbina, W. Voelter, A. Weiler, H. Echner, S. Stoeva,J.P.Schernthaner, W.Reinig, G. Grubler and W. Gross
25. SOLID-PHASE SYNTHESIS OF OLIGONUCLEOTIDE AND PEPTIDEDITHIOPHOSPHATES 141
Peter H. Seeberger, Jennifer L. Jordan, and Marvin H. Caruthers
26. AN EFFICIENT DEPROTECTION STRATEGY FOR AUTOMATEDOLIGONUCLEOTIDE SYNTHESIS USING A NOVEL SILYLLINKED SOLID SUPPORT 147
Anne Routledge, Mark P. Wallis, Kenneth C. Ross and William Fraser
Peptide Libraries / Library Applications (I)
27. COMBINATORIAL CHEMISTRY: PAST AND PRESENT DEVELOPMENTS 151Arpad Furka, Eugen Campian, Mark Peterson, Hossain Saneiiand Joanne Chou
28. THE ZINC FINGER MOTIF AS A CONFORMATION-INDUCING TEMPLATEFOR SELECTION-DRIVEN DESIGN OF PEPTIDOMIMETICS 159
Elisabetta Bianchi, Gaetano Barbato, Andrew Wallace, Riccardo Cortese,Franco Felici, Renzo Bazzo and Antonello Pessi
SYNTHESIS / BIOLOGICAL & BIOMEDICAL APPLICATIONS
Peptide Vaccine Assemblies / Development
29. POLYMER-SUPPORTED COMBINATIONS OF PEPTIDE EPITOPES FROMHIV-1 gP120/gp41 OR FeLV env. - SUGGESTIONS FOR SYNTHETICVACCINE CONSTRUCTS 163
Christian Birr, Klaus Friebel, Gerhard Becker, Sigrid Nick, Gerald Voss,Hubert Bayer and Gerhard Hunsmann
30. NOVEL PEPTIDE TREATMENTS OF IgE ALLERGIES 173Denis R. Stanworth
Advances in Solid Phase Peptide / Protein Synthesis (III)
31. RECENT PROGRESS ON THE FORMATION OF SULFUR-SULFURBRIDGES IN PEPTIDES 181
George Barany and Lin Chen
32. BACKBONE AMIDE (BAL) ANCHRING IN SOLID PHASE PEPTIDESYNTHESIS ...,.-. 187
Knud J. Jensen, Michael F. Songster, Jordi Alsina, Josef Vagner,Fernando Albericio and George Barany
33. NOVEL HIGHLY CROSS-LINKED SUPPORTS FOR SOLID PHASEAPPLICATIONS 191
Maria Kempe and George Barany
34. THE PURIFICATION OF PROTECTED PEPTIDE SEGMENTS 195Paul Lloyd-Williams, Fernando Albericio, Margarida Gairand Ernest Giralt
Peptide Libraries / Library Applications (II)
35. POSITIONAL SCANNING COMBINATORIAL LIBRARIES BUILT AROUNDMONO-AND BICYCLIC PEPTIDE TEMPLATES 201
Jutta Eichler, Adam W. Lucka and Richard A. Houghten
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36. SIMULTANEOUS MULTIPLE SYNTHESIS OF BACKBONE-CYCLIC PEPTIDELIBRARIES 205
Chaim Gilon, Gal Bitan, Irina Zeltser and Dan Muller
37. POTENTIAL APPLICATIONS OF CYCLIC PEPTIDE LIBRARIES 209Philip E. Thompson, Vittoria Cavallaro and Milton T.W. Hearn
38. COMBINATORIAL SYNTHESIS OF PEPTIDE-INTERCALATOR-PEPTIDECONJUGATES 213
Glenn Tong and John Nielsen
Biologically / Biomedically-significant Peptides / Proteins (I)
39. THE ROLE OF PRIMARY AND SECONDARY STRUCTURE IN ANTIBODYRECOGNITION OF A PROTEIN CORE EPITOPE FROM THE TANDEM REPEATUNIT OF MUC2 GLYCOPROTEIN: THE USE OF D-AMINO ACIDSUBSTITUTED FLANKS 217
Katalin Uray, Judit Kajtar, Michael R. Price, Ferenc Hudecz
40. CHEMICAL SYNTHESIS AND BIOLOGICAL ACTIVITY OF RELAXINPEPTIDES 223
John D Wade, Daniela Salvatore, Feng Lin and Geoffrey W Tregear
41. SOLID-PHASE SYNTHESIS OF DIFFERENT GALANINS, THEIR SEGMENTSAND ANALOGS 227
Lajos Balaspiri, Tamas Janaky, Csaba Somlai, Marianna Mak, Jr.Laszlo Otvos,Gabor Blazso, Tamas Takacs and Peter Kasa
Methodology - Application to Large Scale Solid Phase Synthesis
42. SUPPRESSING RACEMIZATION IN THE REGENERATION PROCEDUREOF FMOC-AMINOACID DERIVATIVES RECOVERED FROMPEPTIDE SYNTHESIS 233
Michael Kiffe, Yoshio Yokomizo and Kiyoshi Nokihara
43. HIGH-LOADED SUPPORTS AND THE NPE/NPEOC-STRATEGY:AN EFFICIENT COMBINATION FOR LARGE SCALE SYNTHESISOF OLIGONUCLEOTIDES 239
Jan Weiler and Wolfgang Pfleiderer
44. PHASE CHANGE DURING PEPTIDE SYNTHESIS 243Panagiotis Athanassopoulos, Kleomenis Barlos, Olga Hatzi,Dimitris Gatos and Chryssoula Tzavara
Biologically / Biomedically-significant Peptides / Proteins (II)
45. THE P-THYMOSIN STORY 247Wolfgang Voelter, Khalid Mohammed Khan, Hartmut Echner,Gerald Griibler, Hans Zimmermenn, Rania Tsitsiloniand Stanka Stoeva
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46. NMR STUDIES OF THE 11-RESIDUE CYTOPLASMIC PEPTIDE THATBRIDGES TWO TRANSMEMBRANE HELICES OF THE HIGHAFFINITY IgE RECEPTOR 253
Mire Zloh, Rodplfo R. Biekofsky, Ettore Benedetti, Malcom Danton,Istvan Toth and William A. Gibbons
47. CHEMICAL SYNTHESIS, STRUCTURE AND BIOCHEMICAL FUNCTION OFMYCOBACTERIUM TUBERCULOSIS CHAPERONIN 10 259
G. Fossati, P. Lucietto, H.L. Ball, P. Giuliani, E. Chan, A. Zaliani, G.Legname, S. Harding, H. Colfen, A.R.M. Coates and P. Mascagni
Solid Phase Glycopeptides (I & II) - Opiod Peptides
48. RECENT TECHNIQUES IN GLYCOPEPTIDE SYNTHESIS AND BIOLOGY:THE GLYCOPEPTIDE TEMPLATES , 263
Morten Meldal, Henrik Franzyk, Ernst Meinjohanns,Antonio Vargas-Berenguel, Klaus Frische, Mette Knak Christensen,Ida Christiansen Brams, Knud J0rgen Jensen and Klaus Bock
49. EXPLORING THE DIVERSITY OF MONO- AND OLIGOSACCHARIDESTRUCTURES IN THE SYNTHESIS, CONFORMATIONAL ANALYSISAND BIOMEDICAL APPLICATION OF GLYCOPEPTIDES 269
Laszlo Otvos, Jr., Laszlo Urge, Gyorgyi I. Szendrei, Barbara Cappelletto,Istvan Varga, Katherine Vogele Prammer and Hildegund C.J. Ertl
50. SYNTHESIS AND PHARMACOLOGY OF O-LINKED GLYCOPEPTIDEENKEPHALIN ANALOGUES: A NEW CLASS OF OPIOID ANALGESICS 277
Robin Polt, Lajos Szabo, V. J. Hruby, T. P. Davis, Frank Porrecaand H. I. Yamamura
51. SOLID PHASE SYNTHESIS OF A DIRECTED SMALL ORGANIC LIBRARY:DISCOVERY OF A NEW CLASS OF DELTA OPIOD DRUG LEAD 281
Marguerite M. Letulle, Nathan Collins, Peg Davis, Richard Knapp,Kathy Lee, Hank Yamamura, Frank Porreca and Victor J. Hruby
Biologically / Biomedically-significant Peptides / Proteins (III)
52. DESIGN OF SELECTIVE, FLUOROGENIC SUBSTRATES FOR MEMBERS OFTHE MATRIX METALLOPROTEINASE FAMILY 285
Gregg B. Fields and Michael W. Pennington
53. DETERMINING Sn' SPECIFICITIES OF SERINE PROTEINASES USINGCOMBINATORIAL PEPTIDE LIBRARIES, AND EVIDENCE THATENZYMES CAN PENETRATE TENTAGEL RESIN BEADS 291
Gordon Lowe and Rachel Quarrell
54. A NATURAL a/p SCAFFOLD FOR THE DESIGN AND SYNTHESIS OF NOVELPROTEINS 295
Claudio Vita, Eugenia Drakopoulou, Carole Leon, Sophie Zinn-Justin,Marc Guenneugues and Andre Menez
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POSTER PAPERS
55. SYNTHESIS OF HUMAN GUANYLIN: TEMPERATURE-DEPENDENT HPLC,CZE AND NMR STUDIES VERIFY STEREOISOMERISM OF ADISULFIDE-CONTAINING PEPTIDE 299
Knut Adermann, Susanne Neitz, Ute C. Marx, Paul Roschand Wolf-Georg Forssmann
56. DARAS™ (DNA AND RNA ANALYSIS SYSTEM) 303Ayo A Akinsanya, Simon J Barker, Allan Brown, Ian R Hudson,John D Oultram and Stephen J Minter
57. SYNTHESIS OF CLASS I MAJOR HISTOCOMP AT ABILITY COMPLEXBINDING PHOSPHOPEPTIDES 307
G. Arsequell, J. Haurum, T. Elliot and G. Valencia
58. DESIGN OF INHIBITORS TO THE ATP BINDING SITE OF DNATOPOISOMERASES II 309
Liliane Assairi
59. A NEW VERSATILE CARRIER DERIVED FROM MAP FOR IMMUNOLOGICALSTUDIES 313
Franchise Baleux, Philippe Dubois and Helene Jouin
60. SOLID PHASE SYNTHESIS OF A AND B CHAINS OF HUMAN INSULIN 317E. Bayer, G. Panhaus and M. Ali Khan
61. AUTOMATIC PEPTIDE SYNTHESIZER USEFUL FOR MULTIPLE PEPTIDESYNTHESIS AND PEPTIDE LIBRARIES 319
Ivo Blaha, Martin Flegel, Vera Cerna, Manfred Pavlfk,Vft Pokorny,Petr Mudra, Ludek Lepsa and Karel Zenfsek
62. CYCLIC PEPTIDE SYNTHESIS VIA DISULFIDE BONDS IN GOOD YIELD ANDPURITY - USE OF THE AIR OXIDATION/DIFFUSION METHOD 321
Graham B. Bloomberg, David Askin and Michael J.A. Tanner
63. IMPROVED SYNTHESIS OF DIFFICULT SEQUENCES CONTAINING SERINE ANDTHREONINE WITH FMOC CHEMISTRY 323
Graham B. Bloomberg, William J. Mawby and Michael J.A. Tanner
64. SOLID PHASE COUPLING OF UNPROTECTED REDUCING CARBOHYDRATESTO THE N-TERMINUS OF PEPTIDES 327
Ulrik Boas, Peter Heegaard and Mogens H. Jakobsen
65. ANALYSIS OF THE ANTIGENIC STRUCTURE OF TWO IMMUNODOMINANTREGIONS OF THE 16 KDA PROTEIN OF M. TUBERCULOSIS: ELUCIDATION OFTHE MINIMAL SIZE OF T CELL EPITOPES 329
Katalin A. Bogdan, Martin H. Vordermeier, Stipo Jurcevic, Juraj Ivanyiand Ferenc Hudecz
66. SOLUTION STRUCTURE OF THE GLA DOMAIN OF CLOTTING FACTOR VII BYCIRCULAR DICHROISM; CORRELATION WITH INHIBITORY PROPERTIES 323
P. Byfield, B. Bolgiano, C. Hyde, D. Martin and E. Tuddenham
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67. LARGE-SCALE SOLID-PHASE CONTINUOUS-FLOW PREPARATION OFA 26-MER PEPTIDE THROMBIN INHIBITOR 335
Valerio Caciagli, Franco Cardinali, Fabio Bonelli and Paolo Lombardi
68. SYNTHESIS AND CHARACTERIZATION OF A COMBINATORIAL LIBRARY:APPLICATION TO THE DISCOVERY OF A BRADYKINTN B2 RECEPTORANTAGONIST 339
Sarvajit Chakravarty, Babu J. Mavunkel, Robin Andy and Donald J. Kyle
69. USE OF REDUCED («P[CH2-NH]) AND N-METHYL(vF[CO-N(Me)])PSEUDOPEPTIDES IN BACKBONE SCANNING OF T CELL EPITOPE 341
J. Cotton, A. Lecoq, M. Herve, B. Maillere, S. Leroy and A. Menez
70. NEW APPLICATION OF THE SYNTHETIC BRANCHED MULTIMERICPEPTIDES : MIME OF THE PHYSICOCHEMICAL PROPERTIES OFAPOLIPOPROTEIN A-I , 343
L. Demoor, C. Boutillon, M. Rosseneu, J.C. Fruchart and A. Tartar
71. CHARACTERIZATION OF BINBING SITES OF FIBRIN SPECIFIC MONOCLONALANTIBODIES USING COTTON-BOUND COMBINATORIALPEPTIDE LIBRARIES 347
L. Doleckova, M. Pavlik, Z. Voburka, M. Rinnova, J. Suttnar and J.E. Dyr
72. N-ALKYLATED PEPTIDOMIMETIC COMBINATORIAL LIBRARIES 351Barbara Dorner, Jutta Eichler, Gregory M. Husar, John M. Ostreshand Richard A. Houghten
73. CARBOXAMIDE PROTECTION OF ASPARAGINE AND GLUTAMINE BY10,1 l-DIHYDRO-5H-DIBENZO[A,D]CYCLOHEPTEN-5-YL(SUB) AND5H-DIBENZO[A,D]CYCLOHEPTEN-5-YL(DBS) GROUPS 353
Harmut Echner and Wolfgang Voelter
74. IDENTIFICATION AND SYNTHESIS OF AN ASPARTIMIDE PEPTIDEMODULATING T CELL RECOGNITION OF A SYNTHETICPEPTIDE ANTIGEN , 359
Nicholas J. Ede, Weisan Chen, James McCluskey, David C. Jacksonand Anthony W. Purcell
75. GEL PHASE 13C-NMR MONITORING OF SOLID PHASE GLYCOSIDE SYNTHESISHans-Michael Eggenweiler and Ernst Bayer 363
76. AN APPRAOACH TO THE SYNTHESIS OF ARGININE CONTAINING ,,.. yNUCLEOPEPTIDES VIA MODIFIED PHOSPHOTRIESTER METHODOLOGY ..' 367
D. Filippov, N.J. Meeuwenoord, E. Kuhl-Yeheskiely, J.C.H.M. Wijkmans,G.A. van der Marel and J.H. van Boom
77. PREPARATION OF SYNTHETIC PEPTIDE LIBRARIES USING A MULTI COLUMNPARALLEL-FLOW MPS DEVICE 369
Laura Gazzerro, Massimo Pinori and Paolo Mascagni
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78. 2,4-METHANO AMINO ACIDS, NOVEL CONSTITUENTS OF BIOACTIVEPEPTIDES: TUFTSIN AS A MODEL 373
Eytan Gershonov, Ruth Granoth, Esther Tzehovel, Yehiel Gaoniand Mati Fridkin
79. COMPARISON OF SEVERAL SULFURIZING REAGENTS FOR SYNTHESIS OFPHOSPHOROTHIOATE OLIGONUCLEOTIDES ON DIFFERENT SUPPORTS 377
Michael Gerster, Konrad Bleicher and Ernst Bayer
80. RATIONALLY DESIGNED DIVERSE NON-PEPTIDES: VARIOUSLY SUBSTITUTEDPIPERAZINE AND PIPERAZINEDIONE LIBRARIES TARGETED FOR THEDISCOVERY OF BRADYKININ AND OTHER G-PROTEIN COUPLEDRECEPTOR ANTAGONISTS 381
Val S. Goodfellow, Christopher P. Laudeman, J. Ivan Gerrity,Michael Burkhard, Eric Strobel and Don A. McLeod
81. A NEW SIDE-CHAIN ANCHORING STRATEGY FOR SOLID-PHASE SYNTHESISOF PEPTIDE ACIDS WITH C-TERMINAL CYSTEINE 385
Yongxin Han, Josef Vagner and George Barany
82. STUDIES ON MECHANISM OF PEPTIDE CARBOXY ACTIVATION 389Christiane Hanay, Michael Beyermann and Peter Henklein
83. NEW LIGANDS FOR THE HUMAN MELANOMA MSH RECEPTOR IDENTIFIEDBY A PEPTOID LIBRARY (OLIGO N-SUBSTITUTED GLYCINES) 391
Gerhard Heizmann, Heidi Tanner and Alex N. Eberle
84. p-(5-DIBENZOSUBERENYL-5-HYDROXY)-BENZOIC ACID: A NEW LINKERFOR PEPTIDE SYNTHESIS 395
Bernd Henkel and Ernst Bayer
85. SYNTHESIS OF TRIPLE-HELICAL PEPTIDES INCORPORATING NATIVECOLLAGEN TYPE II SEQUENCES USING A CONTINUOUS FLOWSYNTHESIZER 399
W. Henkel, H. Echner, W. Voelter, U. Bahr and T. Vogl
86. SYNTHESIS, STRUCTURE AND BIOLOGICAL ACTIVITY OF CYCLICCCK-DERIVATIVES 403
Peter Henklein, Hardy WeiBhoff, Roland Kaufmann and Ute Schafer
87. NEW SAFETY-CATCH LINKAGES FOR THE DIRECT RELEASE OF PEPTIDEAMIDES INTO AQUEOUS SOLUTIONS 407
Stefan Hoffmann and Ronald Frank
88. DESIGN AND SYNTHESIS OF FMRF AMIDE-LIKE PEPTIDES AND THEIRAPPLICATION TO STUDY OF PAIN IN THE SPINAL CORD 411
Eagle Yi-Kung Huang, Jeff Bagust, Ram P.Sharma and Robert J. Walker
89. PHOTOCHEMICAL COUPLING OF PEPTIDES TO POLYSTYRENE MICROWELLPLATES 419
S0ren Peter Jensen, Svend Erik Rasmussen and Mogens Havsteen Jakobsen
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90. SOLID PHASE GLYCOPEPTIDE SYNTHESIS OF TYROSINE GLYCOSYLATEDGLYCOGENIN FRAGMENTS 423
Anita M. Jansson, Knud J. Jensen, Morten Meldal and Klaus Bock
91. SOLID PHASE SYNTHESIS OF Tn ANTIGENS IN BOTH FREE ANDIMMOBILIZED FORM 427
Jan Jezek, Jin Velek, Tomas Trnka and Martin Pisacka
92. HORNER-WADSWORTH-EMMONS ALKENE SYNTHESIS ON SOLID PHASEMONITORING BY 31P GEL PHASE NMR 429
Charles R. Johnson and Birong Zhang
93. DIFFICULT PEPTIDE SEQUENCES OF MMIF IN FMOC-CONVERGENT SOLIDPHASE PEPTIDE SYNTHESIS 431
Thomas Kaiser and Wolfgang Voelter
94. FORMATION OF DISULFIDE BOND ON SOLID SUPPORT 435Koichi Kawasaki, Yasuhiro Izuno, Masa Kakiuchi and Mitsuko Maeda
95. USE OF A TENTAGEL SUPPORT IN THE PREPARATION OF ALL SIXTEEN2'-DEOXYDINUCLEOSIDE PHOSPHORODITHIOATES 437
Jan Kehler, Anne B. Eldrup, Jakob Felding and Otto Dahl
96. C-TERMINAL SEQUENCE ANALYSIS OF PEPTIDES 441Weiland Keilholz, Stefan Stevanovic, Daniele Arnoldand Hans-Georg Rammensee
97. MYRISTYLATED NEF PEPTIDE (2-57) FROM HIV TYPE I: SYNTHESIS ANDSTRUCTURAL STUDIES 445
Roland Kellner, Stephan Rawer, Matthias Geyer and Hans R. Kalbitzer
98. THE IDENTIFICATION OF A NON-PEPTIDE GPHB/HIA ANTAGONIST 449J. Kitchin, J. Broomhead, B. Carter, A.J. Crame, M. Foster, M. Hann,E. Hornby, S. Hindley, C. Perry, A.J. Pipe, N.R. Taylor and P. Ward
99. OPTIMIZED PURITY CONTROL OF SYNTHETIC OLIGODEOXYRIBO-NUCLEOTIDES BY CAPILLARY ELECTROPHORESIS FORCLINICAL PCR ASSAY 455
Rainer Lehmann, Mattais Koch, Gerald Griibler, Wolfgang Reinig,Hans Zimmerman, Waleri Gross and Wolfgang Voelter
100. AN EFFICIENT THREE DIMENSIONAL ORTHOGONAL STRATEGY FORSOLID-PHASE SYNTHESIS OF A BIFUNCTIONAL PEPTIDE 459
Dominique Lelievre, David Daguet, Friedrich Piller, Veronique Piller,Cecille Vassard and Andre Brack
101. HSV-2 UNIQUE PEPTIDES WITHOUT SEROLOGICAL CROSS-REACTIVITY 461Ulla Ruden, Michael Levi and Britta Wahren
102. SOLID PHASE POLYAMINE CHEMISTRY - A ROUTE TO ANTI-TRYPANOSOMAL COMPOUNDS 463
Ian R. Marsh and Mark Bradley
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103. SELECTION OF PROTEINASE INHIBITORS FROM A CONFORMATIONALLY-CONSTRAINED COMBINATORIAL PEPTIDE LIBRARY 465
Jeffrey D. McBride, Neil Freeman, Gonzalo J. Domingoand Robin Leatherbarrow
104. THE IMPORTANCE OF PEPTIDE SOLVATION IN THE SYNTHESIS OF A PEPTIDEANALOGUE OF THE 2A REGION OF THE FOOT AND MOUTH DISEASE VIRUSGENOME SHOWN BY CONDUCTIVITY MONITORING 469
Brendan McKeown, David J.S. Guthrie, Neil V. McFerran,Martin D. Ryan and Brian Walker
105. COMPARATIVE STUDIES OF METHOXY-SUBSTITUTED 4-BENZYLOXY-TRITYLAMINE LINKERS FOR SOLID PHASE SYNTHESIS OFPROTECTED PEPTIDE AMIDES 473
Mark Meisenbach and Wolfgang Voelter
106. SOLID PHASE SYNTHESIS OF PEPTIDE FRAGMENTS OF HUMAN RELAXINFOR THE ISOLATION OF SPECIFIC ANTIBODIES 477
Mark Meisenbach, Franz-Paul Armbruster, Stephan Becker,Theodor H. Lippert, Gerd Paulus, Hans-Jiirgen Kohlbau,Gerald Griibler and Wolfgang Voelter
107. RAPID SYNTHESIS OF FULLY PROTECTED PEPTIDE AMIDES 481M. Mergler and R. Nyfeler
108. SYNTHESIS OF SAPECIN EMPLOYING REGIOSELECTIVE DISULPHIDE BONDFORMATION 485
M. Mergler and R. Nyfeler
109. SOLID PHASE SYNTHESIS OF ENDOTHIOPEPTIDES USING 3-(N-a-BOCAMINOTHIOACYL)-l,3-THIAZOLIDINE-2-THIONES, NEW EFFICIENTTHIOACYLATING AGENTS 487
Robert J. Michelot, Hoang-Thanh Le and Michel Mayer
110. ANTISERA DIRECTED AGAINST SYNTHETIC PEPTIDES RECOGNIZE THENATIVE CCK-A RECEPTOR 489
Corinna Morys-Wortmann, Laurence J. Miller, Klaus Nebendahland Wolfgang E. Schmidt
111. A NOVEL STRATEGY FOR THE SYNTHESIS OF HEME-PEPTIDECONJUGATES : 491
Flavia Nastri, Angela Lombardi, Ornella Maglio, Giancarlo Morelli, GabbriellaD'Auria, Carlo Pedone and Vincenzo Pavone
112. SIDE REACTIONS ASSOCIATED WITH PHOSPHOPEPTIDE SYNTHESIS 495Elizabeth A. Ottinger, Quighong Xu andGeorge Barany
113. SPATIALLY ADDRESSABLE LIGATION ASSAYS: APPLICATION OFOLIGONUCLEOTIDE ARRAYS TO DNA FINGERPRINTING 499
Clare E. Pritchard and Edwin M. Southern
114. GLYCOPEPTIDE SYNTHESIS OF GPIIb (843-854) AND BOVINEFETUIN (152-164) 503
Stephan Rawer, Knut Adermann and Wolf-Georg Forssmann
115. LIPOSOMES AS CARRIERS FOR PEPTIDES IN CANCER THERAPY 505Francesca Reig, Isabel Haro, Liuis A. Lopez Barcons, E. Grieraand Angels Fabra
116. USE OF METHYL RED IN SOLID PHASE SYNTHESIS 509Marketa Rinnova, Martin Fusek and Michal Lebl
117. STRUCTURE-AFFINITY STUDIES OF CYCLIC DODEKAPEPTIDE ANALOGUESOF NEUROPEPTIDE Y 511
B. Rist, H.A. Wieland, K-D. Willim and A.G. Beck-Sickinger
118. CYCLIZATIONS OF PEPTIDES AND OLIGOAMIDES BOUND TO SILICA GELAS A RIGID SUPPORT 515
M. Rothe, A. Negele, T. Mohr and S. Kneer
119. PSEUDO-PROLINES IN PEPTIDE SYNTHESIS: TEMPORARY TURN INDUCTIONAND CONFORMATIONAL RESTRICTION 519
Declan Ryan, Pascal Dumy, Ian M. Eggleston and Manfred Mutter
120. DE NOVO LEAD IDENTIFICATION AGAINST GLYCOSOMALPHOSPHOGLYCERATE KINASE 523
Isabell Samson, Arthur Van Aerschot, Bart Samyn, Jozef Van Beeumenand Piet Herdewijn
121. DIESTER BUILDING BLOCKS OF pSER AND pTHR SUITABLE FOR FMOCSOLID PHASE PEPTIDE SYNTHESIS 525
Holger Schmid, Stefan Vetter, Willi Bannwarth and Eric Kitas
122. MATRIX-DEPENDENT DEPROTECTION OF PEPTIDE FRAGMENTS DURINGMALDI-TOF MASS SPECTROMETRY 529
Margit Schmidt, Eberhard Kraus, Michael Beyermann and Michael Bienart
123. USE OF THE Hmb BACKBONE PROTECTING GROUP IN THE SYNTHESIS OFDIFFICULT SEQUENCES 533
Robin G. Simmonds
124. NOVEL HANDLES FOR SOLID PHASE SYNTHESIS OF PEPTIDEN-ALKYLAMIDES 537
Michael F. Songster, Josef Vagner and George Barany
125. SYNTHESIS AND FOLDING OF co-CONOTOXINS 539Linda Thomas, Paul F. Alewood and Richard J. Lewis
126. SYNTHESIS OF NEW CHIRAL PNA ANALOGUES 543A.C. van der Laan, I. van Amsterdam, R.S. Oosting, R. Brands,N.J. Meeuwenoord, E. Kuyl-Yeheskiely and J.H. van Boom
xvm
127. PROTECTED PEPTIDE INTERMEDIATES USING A TRITYL LINKER ONA SOLID SUPPORT 545
Alexandra van Vliet and Godefridus I. Tesser
128. SOLID PHASE SYNTHESIS OF [4/Pro-7]SARAFOTOXIN-S6b APPLYINGTHE CONCEPT OF PSEUDO-PROLINES 549
Frank Wahl, Barbara Rohwedder, Nathalie Berclaz and Manfred Mutter
129. TOPOGRAPHICAL MIMICS OF A STRUCTURED PEPTIDE SELECTED FROMA CONFORMATIONALLY-HOMOGENEOUS PEPTIDE COMBINATORIALLIBRARY 553
Andrew Wallace, Elisabetta Bianchi, Michael Houston, Robert Hodgesand Antonello Pessi
130. PREPARATION OF PHOSPHOSERINE, THREONINE AND TYROSINECONTAINING PEPTIDES BY THE FMOC METHODOLOGY USING PRE-FORMEDPHOSPHOAMINO ACID BUILDING BLOCKS 557
P. White and J. Beythien
131. JV-DITHIASUCCINOYL (DTS)-AMINES: NOVEL SULFURIZING REAGENTSFOR THE SOLID PHASE PREPARATION OF THIOPHOSPHOPEPTIDES ANDOLIGODEOXYRIBONUCLEOSIDEPHOSPHOROTHIOATES 561
Qinghong Xu, Karin Musier-Forsyth, Robert P. Hammer and George Barany
132. INTRAMOLECULAR DISULFIDE BOND FORMATION ON THE SOLID SUPPORT:SYNTHESIS OF RGDF-CONTAINING CYSTINE PEPTIDES 565
Yasuo Yamamoto and Shosuke Sofuku
133. PEPTIDE ENGINEERING FOR VACCINES THROUGH POLYOXIMECHEMISTRY : '. 567
Weiguang Zeng, Keith Rose and David C. Jackson
134. SOLID PHASE SYNTHESIS OF THE FULLY PROTECTED NEPHRITOGENOSIDEGLYCOPEPTIDE 573
Hong Zhang, Yali Wang and Wolfgang Voelter
Abbreviations 575
Author Index 578
Subject Index 583