"Kombinatorische Chemie und Festphasensynthese " Ulrich Jordis Inst. Für Angewandte Synthesechemie 2006

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1 "Kombinatorische Chemie und Festphasensynthese " Ulrich Jordis Inst. Für Angewandte Synthesechemie

2 Historical Landmarks 1963: Merrifield: peptide on polystyrene resin 1965: Letsinger and Khorana: ligonucleotides 1974: F. Camps: Synthesis of Benzodiazepines on sold support 1996: Ugi four component reaction in combination with 1,3-dipolar cycloaddition 2

3 Literatur: Bücher D. lbrecht, J.M. Villalgordo: Solid-Supported Combinatorial and Parallel Synthesis of Small- Molecular-Weight Compound Libraries Pergamon 1998 Barry A. Bunin: The Combinatorial Index Academic Press 1998, 322 S. S. R. Wilson, A. W. Czarnik: Combinatorial Chemistry, J. Wiley 1997, 269 S. A. W. Czarnik, S. H. DeWitt: A Practical Guide to Combinatorial Chemistry, ACS 1997, 450 S.. K. Terret: Combinatorial Chemistry, xford Univ. Press 1998, 186 S. Literatur: Bücher II Günther Jung, Ed.: Combinatorial Chemistry Synthesis, Analysis, ScreeningWiley-VCh 1999 M. R. Pavia and W. H. Moos: Annual Reports in Combinatorial Chemistry and Molecular Diversity Vol. 2, Kluwer Academic Publishers, 1999 Advanced ChemTech Handbook of Combinatorial & Solid Phase rganic Chemistry VABICHEM: Solid Phase rganic Chemistry Handbook 3

4 Literatur: Bücher III Combinatorial Chemistry: A Practical Approach by Willi Bannwarth, Eduard Felder, Raimund Mannhold, Hugo Kubinyi, Hendrik Timmerman - Wiley-VCH Literatur: Datenbanken Solid Phase rganic Reactions (SPRE) ISIS/Host (MDL) >6.000 reactions contains extensive data from solid-phase organic chemistry, including polymeric materials, linkers, solid supports, and protecting groups. Synopsys Solid-Phase Synthesis (SPS) ca reactions from more than 1,673 citations including patents 4

5 The Integrated Approach Biochemistry Genomic Science Molecular Biology Target Identification and Selection: Enzymes Receptors Transcription Factors Protein Expression and Purification Rational and Random Design Protein Expression and Purification Structure Determination (X-Ray, 2D- and 3D-MR) Cocrystallization of Ligand and Target Protein Structure Based "de novo" Design Lead / Ligand ptimization Assay Development High Throughput Screening (HTS) Lead / Ligand Identification Combinatorial Compound Libraries Development Compound 5

6 Types of Libraries Catalyst Development Ligand Design Drug Discovery Lead Finding Lead ptimization Peptides Proteins ucleotides licosaccharides Antibodies High Temp. Supraconductors Inks& Dyes Productivity traditional 6

7 Combinatorial Libraries Combinations (1) A1-B1-C1 -C2 -C3 A1-B2-C1 -C2 -C3 A1-B3-C1 -C2 -C3 A2-B1-C1 -C2 -C3 A2-B2-C1 -C2 -C3 A2-B3-C1 -C2 -C3 A3-B1-C1 -C2 -C3 A3-B2-C1 -C2 -C3 A3-B3-C1 -C2 -C3 A B C, only one linear assembly possible: A B C 3 X 3 X 3 = 27 combinations 7

8 Combinations (2) A1-B1-C1 -C2 -C3 A1-B2-C1 -C2 -C3 A1-B3-C1 -C2 -C3 A2-B1-C1 -C2 -C3 A2-B2-C1 -C2 -C3 A2-B3-C1 -C2 -C3 A3-B1-C1 -C2 -C3 A3-B2-C1 -C2 -C3 A3-B3-C1 -C2 -C3 A B C, six linear permutations possible: A B C A C B B A C B C A C A B C B A 3 X 3 X 3 X 6 = 162 combinations Combinations (3) A B C A B C A B C A B C A B C ne directed sequence: 3 X 3 X 3 = 27 combinations All cyclic permutations: 3 X 3 X 3 X 2 = 54 combinations 8

9 umber of different peptides increases exponentially with the length of the molecule umber of amino acid residues umber of distinct peptides Peptide 2 H2-X1X2-CH H2-X1X2X3-CH H2-X1X2X3X4-CH H2-X1X2X3X4X5-CH H2-X1X2X3X4X5X6-CH H2-X1X2X3X4X5X6X7-CH H2-X1X2X3X4X5X6X7X X = 20 natural amino acids umbers Traditional- / Array- / ne-pot simultaneous- / Indexed Comb. Lib. Synthesis 9

10 Indexed, rthogonal Combinatorial Libraries Komponenten der Bibliothek 10

11 Test der Mischungen Indexed (=rthogonal) Combinatorial Libraries 1A-1H 2C 2A-2H 3A-3H 4A-4H 5A-5H 6A-6H A1-A6 B1-B6 C1-C6 D1-D6 E1-E6 F1-F6 G1-G6 H1-H6 Pirrung, M.C. et.al., Chem. Biol. 1995, 2,

12 rthogonal Libraries A1B1 A2B1 A3B1 A4B1 A1B2 A2B2 A3B2 A4B2 A1B3 A2B3 A3B3 A4B3 A1B1 A1B2 A1B3 A2B1 A2B2 A2B3 A3B1 A3B2 A3B3 A4B1 A4B2 A4B3 A1B1 A2B1 A3B1 A4B1 A1B2 A2B2 A3B2 A4B2 A1B3 A2B3 A3B3 A4B4 Deconvolution 12

13 Scaffold Survey Cl H H H 3 C H CH 3 CH 3 H 3 C H H H H H 3 C Antiviral (AIDS) (Roche) S H H CHHS 3 H 2 Alcohol Deterrent (Biomeasure) C H 3 Cl S Cl Uterine Relaxant; xytocin Antagonist (Merck & Co.) H 3 C CH 3 H H S H Antiulcerative; Pancreas Disorders; CCK Antagonist (Jouveinal) H 3 C H H H S Farnesyltransferase Inhibitor; Antineoplastic (Genentech) Anxiolytic; Anticonvulsant (Gerardo Ramon) Antiarthritic; Gastrin Antagonist; Anxiolytic; CCK Antagonist (Merck & Co.) CCK Antagonist; on-pioid Analgesic; Anxiolytic (Merck & Co.) # Specific Structures: 2520 MWT Range: Virtual Library R3 R2 H R1 R1= C S F F F Cl S S S Cl S R2= C H F R3= H C 13

14 Manual Synthesizer Robotics: A Zymark Robot 14

15 Zymark Robot 15

16 Solid Supports Crosslinked rganic Polymers Linear rganic Polymers Dendrimers Inorganic Supports insoluble in organic solvents microporous, gels macroporous usually soluble in organic solvents solubility depends on size and shape porous glass, Si 2, Al 2 3, clays, graphite Solid Supports: Linkers 16

17 Dendrites as new types of Polymers Dendrites 17

18 Measuring yields loading Loading: mmol functional group / g resin (typisch: mmol/g) Yield: loading of product/loading of starting material 18

19 Solid Phase Synthesis: Analytical Techniques Produkt an Polymer gebunden: Elementaranalyse Titration reaktiver Gruppen Analyse nach Abspaltung: HPCL, GC, CE, IR, MR, MS... Erfahrung lehrt, daß jeder Reaktionsschritt analytisch verifiziert werden muß! Single bead Analysis μg mit ~400 pmol Verbindung Matrix assisted laser desorption (MALDI) Molecular weight imaging using time-offlight secondary ion MS FTIR microscopy: ester carbonyl detected from 130 fmol of material (~0.025% of total bead loading) 19

20 Encoding of Beads Deconvolution problem! Encoding: synthesis history is recorded on the bead - one compound per bead Molecular tags (chemisches Etikettieren) Radiofrequency encoding Laser optical synthesis chip (LSC) Isotope encoding Peptide tags ligon cleotide tags Encoding / Molecular Tags Analyse durch electron capture gas chromatography (ECC) 20

21 Encoding / Molecular Tags Encoding / Radiofrequency 21

22 Encoding / Radiofrequency Encoding / Laser ptical Synthesis Chip (LSC) lasergeritzter 2D Strichcode auf keramischem Grundkörper PS Copolymer als Träger für Festphasen- Synthese Chip: 10 x 10 x 2 mm, Beladungsdichte 5-8 μmol / Chip 22

23 PS-PEG Tantacle Resin PE=Polyoxyethylen PS-PEG Tantacle Resin: Gelphase 23

24 Single-Bead Gelphase 1 H-MR HPLC and GC/MS of single beads 24

25 Photoacoustic FT-IR (two beads) Photoacoustic FT-IR Attenuated total reflection (ATR) IR: IR beam can penetrate bead 1-2 μm Photoacoustic spectroscopy (PAS): IR beam can penetrate bead μm Ion Cyclotron Resonance (ICR) MS Allows detection of masses with high accuracy, e.g. m/z calc.: , found:

26 Ion Cyclotron Resonance (ICR) MS MAS MR spinning at ~2 khz Varian ano-mr probe: < 40 μl 3,5-dimethoxy- 13 C-benzoic acid: ~800 pmol / sample direct 1 H MR from nmol / sample MAS: Magic Angle Spinning 26

27 Gel Phase 13 C-MR 13 C enriched) of single 740 μm Boc-Ala-Val-Ala bead Solid Phase Synthesis: Scheme 27

28 Solid Phase Synthesis: FT-IR of Polymer Solid Phase Synthesis: GC analysis of library 28

29 Solid Phase Synthesis: Single-bead GC/MS Swelling Capacity Solvent crosslinked PS (1% DVB) Merrifield resin (2% DVB) MeH/EtH AcH - 1 MeC 2 - Pyridine - 3 DMF THF, Dioxane Ether 2.6 CH2Cl2 5.2 Toluene

30 Chloromethylated Polystyrenes Chloromethylated PS (2) CH 2 CH 2 CH 2 H 3 C styrene, DVB Cl CH 3 styrene, DVB CH 2 CH 2 DVB C H 3 CH3 CH 3 BCl 3, CCl 4,, 2h acl, CHCl 3 or ClCH 2 CH 2 Cl, Bn + Et 3 Cl - ; S 2 Cl 2, AIB, 60 Cl 30

31 Functionilised PS Resins -CH2Cl further reactions (nucleophilic displacement) -CH2H2 -from Polystyrene (PS) Friedel-Crafts Alkylation Sulfonation, itration Bromination Lithiation From Merrifield-Type Resins (1) 1% DVB, mmol Cl/g: KAc, DMA, 85, 24 h H 3 C CH 3 H 3 C Cl LiAlH 4, Et 2, r.t., 4 h or H 2 H 2, DMF, r.t., 76 h 2% DVB, 2.8 mmol/g: KH, 1-pentanol, reflux, 24 h H 3 C H 31

32 From Merrifield-Type Resins (2) 1% DVB, 3.5 mmol Cl/g: thiourea, dioxane/eth (4:1), 85, 15 h H 3 C S H HBr H 2 KH, EtH/dioxane Cl SH H 3 C H 3 C 1% DVB, 1.15 mmol/g: KSAc, DMF S CH 3 LiBH 4 / Et 2 From Merrifield-Type Resins (3) 2% DVB, 1.36 mmol Cl/g: ac, DMF, H 2 H 2 S 4, AcH, H 2 120, 20 H H H 3 C Cl 2% DVB, 1.05 mmol/g: DMS, ahc3, 155, 6 h H 1,2-dimethoxyethane, m-cpba, 55, 19 h 2% DVB, 6.7 mmol/g: ClPPh2, Li, THF P 32

33 Aminomethylated PS Friedel-Crafts Acylation of PS Trityl xim Photolabile o-nitrobenzhydryl 33

34 Bromination / Lithiation nbuli, hexane or toluene, 60, 3 h Bromination: PS 1% DVB, Br 2, Tl(Ac) 3 or FeCl 3 CCl 4. Br 2, or Br 2, BF 3, nitromethane, r.t. 18 h -BuLi, cyclohexane, TMEDA, 65, 4.5 H itration, Sulfonation 34

35 From PS-Lithium (1) From PS-Lithium (2) 35

36 Polyacrylamide Resins C H 2 CH 3 CH 3 C H 2 H H CH 2 C H 2 H H CH 2 C H 2 CH 3 CH3 TentaGel Resins ethylene oxide Propylene oxide, SnCl 4, CH 2 Cl 2 Ethylene oxide, KH, dioxane,

37 ovel Polymeric Supports: PEGA ovel Polymeric Supports (2): CLEAR 37

38 Solid Supported Reagents: Side Reactions Solid Supported Reagents: Amberlyst - anionic nucleophiles, oxidants or reducing agents 38

39 Synthesis Robot 39

40 Synthesis Robot Combination of Software and Hardware Reaction Block: -40 to 150 C, Filtration, Washing Elevated, programmed stirring Inert Gas / Vacuum / Pressure Fluid Handling Software 40

41 MultiSynTech SyRo Chemfile Editor 41

42 Von der klassischen Vorschrift zum Chemfile 42

43 Reagent Library Building Blocks 43

44 tuwien.ac.at/combichem/index.htm tuwien.ac.at/combichem/references.htm 44

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