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Chloromethyl Polystyrene

€ 83,00*

SIZE
200 - 400 mesh
Capacity
0.8 - 1.4 mmol/g
Product number
 H40001.25G

Product information

The Merrifield resin has in the past been the standard support for the synthesis of peptide acids by Boc strategy. Originally, the cesium salt of a protected amino acid was anchored to the chloromethyl support via nucleophilic displacement of chlorine. Although, Me4N salts, sodium salts in THF with Bu4NF catalysis and more recently zinc salts in EtOH have also been used. Cleavage is normally effected by treatment with HF or trifluoromethanesulfonic acid or by hydrogenolysis, alcohols can be released by using diisobutylaluminium hydride or LiBH4. For cleavage scavengers may be required. New isomeric trialkoxybenzylamine resins have been developed by coupling phthalimidomethyl-3,5-dimethoxyphenols to this resin followed by subsequent treatment with hydrazine, that allows DCC coupling with the carboxyl function of amino acids or peptides. The addition of alcohols can be performed by heating the corresponding potassium or sodium alkoxide and the resin in DMF. Reductive cleavage of the anchoring ester linkage was also accomplished.
Attachment of sodium dihydrocinnamate to this resin and treatment with a solution of lithium diisopropylamide (LDA) in THF formed a resin-bound zinc enolate for aldol condensations. Reductive cleavage with diisobutylaluminium hydride afforded a 1,3-diol library. The removal of ß-lactams has been achieved by using aluminium chloride. Another application of this support to nonpeptides involved anchoring the cesium salts of bromo or iodobenzoic acids followed by subsequent transformation into biaryl derivatives using Suzuki coupling conditions. The products were released from the resin via nucleophilic attack with methoxide ion to give methyl esters.

Literature

L 33 Merrifield Resin

  1. Bodanszky M., Hausner Y. S., Ondetti M. A. in Peptide Synthesis, (Gross E., Meienhofer J., Eds.), Academic Press, Y. Wiley, New York, 1976.
  2. Barany, G. and Merrifield, R. B. Solid-phase peptide synthesis, in The Peptides. Analysis, Synthesis, Biology, Vol 2 (Gross, E. and Meienhofer, J., Eds.), Academic, New York, 1980, 1-284
  3. Gisin, B. F. The preparation of Merrifield-resins through total esterification with cesium salts. Helv. Chim. Acta 1973, 56 (5), 1476-1482. doi: 10.1002/hlca.19730560503.
  4. Loffet, A. Improvement to the Esterification Procedure Used in Solid Phase Peptide Synthesis. Int. J. Protein Res. 1971, 3 (5), 297-299. doi: 10.1111/j.1399-3011.1971.tb01723.x.
  5. Wang, S.-S. Solid-Phase Synthesis of Protected Peptide Hydrazides. Preparation and Application of Hydroxymethyl Resin and 3-(p-Benzyloxyphenyl)-1,1-Dimethylpropyloxycarbonylhydrazide Resin. J. Org. Chem. 1975, 40 (9), 1235-1239. doi: 10.1021/jo00897a011.
  6. Kurth, M. J.; Ahlberg Randall, L. A.; Chen, C.; Melander, C.; Miller, R. B.; McAlister, K.; Reitz, G.; Kang, R.; Nakatsu, T.; Green, C. Library-Based Lead Compound Discovery: Antioxidants by an Analogous Synthesis/Deconvolutive Assay Strategy. J. Org. Chem. 1994, 59 (20), 5862-5864. doi: 10.1021/jo00099a008.
  7. Anuradha, M. V.; Ravindranath, B. Ultrasound in Peptide Synthesis. 3 Zinc-Salt Assisted Anchoring of Carboxylic Acids to Merrifield Resin. Tetrahedron 1995, 51 (19), 5671-5674. doi: 10.1016/0040-4020(95)00230-6.
  8. Schlatter, J. M.; Mazur, R. H. Hydrogenation in Solid Phase Peptide Synthesis. I. Removal of Product from the Resin. Tetrahedron Lett. 1977, 18 (33), 2851-2852. doi: 10.1016/s0040-4039(01)83091-4.
  9. Stewart JM, Morris DH, Synthesis of peptide alcohols by the solid phase method, U.S. Patent 4,254,023, US Patent Office, 1981.
  10. Worster, P. M.; McArthur, C. R.; Leznoff, C. C. Asymmetric Synthesis of 2-Alkylcyclohexanones on Solid Phases. Angew. Chem. Int. Ed. Engl. 1979, 18 (3), 221-222. doi: 10.1002/anie.197902211.
  11. Mata, E. G. Β-Lactams on Solid Support: Mild and Efficient Removal of Penicillin Derivatives from Merrifield Resin Using Aluminum Chloride. Tetrahedron Lett. 1997, 38 (36), 6335-6338. doi: 10.1016/s0040-4039(97)01457-3.

L 24 Library Overview

  1. Furka, et al., 10th Int. Symp. Med. Chem., Budapest, 1988.
  2. Furka, A.; Sebestyén, F.; Asgedom, M.; Dibó, G. General Method for Rapid Synthesis of Multicomponent Peptide Mixtures. Int. J. Pept. Protein Res. 1991, 37 (6), 487-493. doi: 10.1111/j.1399-3011.1991.tb00765.x.
  3. Furka, et al., 14th Int. Cong. of Biochem., Prague, (1988).
  4. Lam, K. S.; Salmon, S. E.; Hersh, E. M.; Hruby, V. J.; Kazmierski, W. M.; Knapp, R. J. A New Type of Synthetic Peptide Library for Identifying Ligand-Binding Activity. Nature 1991, 354 (6348), 82-84. doi: 10.1038/354082a0.

L 25 Libraries

  1. Lebl, M.; Krchnák, V.; Sepetov, N. F.; Seligmann, B.; Strop, P.; Felder, S.; Lam, K. S. One-Bead-One-Structure Combinatorial Libraries. Biopolymers 1995, 37 (3), 177-198. doi: 10.1002/bip.360370303.
  2. Salmon, S. E.; Lam, K. S.; Lebl, M.; Kandola, A.; Khattri, P. S.; Wade, S.; Pátek, M.; Kocis, P.; Krchnák, V.; Thorpe, D. Discovery of Biologically Active Peptides in Random Libraries: Solution-Phase Testing after Staged Orthogonal Release from Resin Beads. Proc. Natl. Acad. Sci. U. S. A. 1993, 90 (24), 11708-11712. doi: 10.1073/pnas.90.24.11708.
  3. Lebl, M.; Krchňák, V.; Salmon, S. E.; Lam, K. S. Screening of Completely Random One-Bead One-Peptide Libraries for Activities in Solution. Methods 1994, 6 (4), 381-387. doi: 10.1006/meth.1994.1038.
  4. Lam, K. S.; Zhao, Z.-G.; Wade, S.; Krchnák, V.; Lebl, M. Identification of Small Peptides That Interact Specifically with a Small Organic Dye. Drug Dev. Res. 1994, 33 (2), 157-160. doi: 10.1002/ddr.430330212.
  5. Nikolaiev V., Stierandová A., Krchñák V., Seligmann B., Lam K.S., Salmon S.E., Lebl M. Peptide-encoding for structure determination of nonsequenceable polymers within libraries -- *Peptide Research, *1993, 6 (3), 161-170.
  6. Lebl, M.; Pátek, M.; Kocis, P.; Krchnák, V.; Hruby, V. J.; Salmon, S. E.; Lam, K. S. Multiple Release of Equimolar Amounts of Peptides from a Polymeric Carrier Using Orthogonal Linkage-Cleavage Chemistry. Int. J. Pept. Protein Res. 1993, 41 (2), 201-203. doi: 10.1111/j.1399-3011.1993.tb00132.x.
  7. Vágner J., Krchñák V., Sepetov N. F., Strop P., Lam K. S., Barany G., Lebl M. Novel Methodology for Differentiation of "Surface" and "Interior" Areas of Polyoxyethylene-Polystyrene (POE-PS) Supports: Application to Library Screening Procedures in Innovation and Perspectives in Solid Phase Synthesis and Related Technologies, Collected Papers, Third Int. Symp. Oxford, England, (Epton R., Ed.), 1994, 347-352.
  8. Lebl M., Krchñák V., Sepetov N. F., Nikolaiev V., Stierandová A., Safar P., Seligmann B., Strop P., Lam K. S., Salmon S. E. One Bead - One Structure Libraries in Innovation and Perspectives in Solid Phase Synthesis and Related Technologies, Collected Papers, Third Int. Symp. Oxford, England, (R. Epton, Ed.), 1994, 233-238.
  9. Lebl M., Krchñák V., Safar P., Stierandová A., Sepetov N. F., Kocis P., Lam K. S., Construction and Screening of Libraries of Peptide and Non-Peptide Structures in *Techniques in Protein Chemistry: V.5; Crabb, J. W., Series Ed.; Academic Press: San Diego, CA,* 1994, 541.
  10. Kočiš, P.; Krchňák, V.; Lebl, M. Symmetrical Structure Allowing the Selective Multiple Release of a Defined Quantity of Peptide from a Single Bead of Polymeric Support. Tetrahedron Lett. 1993, 34 (45), 7251-7252. doi: 10.1016/s0040-4039(00)79300-2.
  11. Torneiro, M.; Still, W. C. Sequence-Selective Binding of Peptides in Water by a Synthetic Receptor Molecule. J. Am. Chem. Soc. 1995, 117 (21), 5887-5888. doi: 10.1021/ja00126a043.
  12. Wennemers, H.; Still, W. C. Peptide Complexation in Water. Tetrahedron Lett. 1994, 35 (35), 6413-6416. doi: 10.1016/s0040-4039(00)78233-5.
  13. Youngquist, R. S.; Fuentes, G. R.; Lacey, M. P.; Keough, T. Generation and Screening of Combinatorial Peptide Libraries Designed for Rapid Sequencing by Mass Spectrometry. J. Am. Chem. Soc. 1995, 117 (14), 3900-3906. doi: 10.1021/ja00119a002.
  14. Wenschuh, H.; Beyermann, M.; Rothemund, S.; Carpino, L. A.; Bienert, M. Multiple Solid Phase Synthesis via Fmoc-Amino Acid Fluorides. Tetrahedron Lett. 1995, 36 (8), 1247-1250. doi: 10.1016/0040-4039(94)02487-v.
  15. Baldwin, J. J.; Burbaum, J. J.; Henderson, I.; Ohlmeyer, M. H. J. Synthesis of a Small Molecule Combinatorial Library Encoded with Molecular Tags. J. Am. Chem. Soc. 1995, 117 (20), 5588-5589. doi: 10.1021/ja00125a022.
  16. Virgilio, A. A.; Ellman, J. A. Simultaneous Solid-Phase Synthesis of .Beta.-Turn Mimetics Incorporating Side-Chain Functionality. J. Am. Chem. Soc. 1994, 116 (25), 11580-11581. doi: 10.1021/ja00104a053.
  17. Fenniri, H.; Janda, K. D.; Lerner, R. A. Encoded Reaction Cassette for the Highly Sensitive Detection of the Making and Breaking of Chemical Bonds. Proc. Natl. Acad. Sci. U. S. A. 1995, 92 (6), 2278-2282. doi: 10.1073/pnas.92.6.2278.
  18. Forman, F. W.; Sucholeiki, I. Solid-Phase Synthesis of Biaryls via the Stille Reaction. J. Org. Chem. 1995, 60 (3), 523-528. doi: 10.1021/jo00108a010.
  19. Look, G. C.; Murphy, M. M.; Campbell, D. A.; Gallop, M. A. Trimethylorthoformate: A Mild and Effective Dehydrating Reagent for Solution and Solid Phase Imine Formation. Tetrahedron Lett. 1995, 36 (17), 2937-2940. doi: 10.1016/0040-4039(95)00442-f.
  20. Rano, T. A.; Chapman, K. T. Solid Phase Synthesis of Aryl Ethers via the Mitsunobu Reaction. Tetrahedron Lett. 1995, 36 (22), 3789-3792. doi: 10.1016/0040-4039(95)00607-e.
  21. Krchňák, V.; Flegelová, Z.; Weichsel, A. S.; Lebl, M. Polymer-Supported Mitsunobu Ether Formation and Its Use in Combinatorial Chemistry. Tetrahedron Lett. 1995, 36 (35), 6193-6196. doi: 10.1016/0040-4039(95)01247-f.
  22. Yan, B.; Kumaravel, G.; Anjaria, H.; Wu, A.; Petter, R. C.; Jewell, C. F., Jr; Wareing, J. R. Infrared Spectrum of a Single Resin Bead for Real-Time Monitoring of Solid-Phase Reactions. J. Org. Chem. 1995, 60 (17), 5736-5738. doi: 10.1021/jo00122a077.
  23. Hauske, J. R.; Dorff, P. A Solid Phase CBZ Chloride Equivalent - a New Matrix Specific Linker. Tetrahedron Lett. 1995, 36 (10), 1589-1592. doi: 10.1016/0040-4039(95)00095-t.
  24. Pátek, M.; Drake, B.; Lebl, M. Solid-Phase Synthesis of “Small” Organic Molecules Based on Thiazolidine Scaffold. Tetrahedron Lett. 1995, 36 (13), 2227-2230. doi: 10.1016/0040-4039(95)00261-a.
  25. Sucholeiki, I. Solid-Phase Photochemical C-S Bond Cleavage of Thioethers-a New Approach to the Solid-Phase Production of Non-Peptide Molecules. Tetrahedron Lett. 1994, 35 (40), 7307-7310. doi: 10.1016/0040-4039(94)85300-2.
  26. Pátek, M.; Drake, B.; Lebl, M. All-Cis Cyclopentane Scaffolding for Combinatorial Solid Phase Synthesis of Small Non-Peptide Compounds. Tetrahedron Lett. 1994, 35 (49), 9169-9172. doi: 10.1016/0040-4039(94)88456-0.
  27. Nielsen J., Brenner S., Janda K. D.Nielsen J, Brenner S, Janda KD. Synthetic methods for the implementation of encoded combinatorial chemistry. J. Am. Chem. Soc. 1993; 115 (21), 9812–9813. doi: 10.1021/ja00074a063.
  28. Campbell, D. A.; Bermak, J. C.; Burkoth, T. S.; Patel, D. V. A Transition State Analog Inhibitor Combinatorial Library. J. Am. Chem. Soc. 1995, 117 (19), 5381-5382. doi: 10.1021/ja00124a030.
  29. Murphy, M. M.; Schullek, J. R.; Gordon, E. M.; Gallop, M. A. Combinatorial Organic Synthesis of Highly Functionalized Pyrrolidines: Identification of a Potent Angiotensin Converting Enzyme Inhibitor from a Mercaptoacyl Proline Library. J. Am. Chem. Soc. 1995, 117 (26), 7029-7030. doi: 10.1021/ja00131a037.
  30. Nicolaou, K. C.; Xiao, X.-Y.; Parandoosh, Z.; Senyei, A.; Nova, M. P. Radiofrequenz-verschlüsselte kombinatorische Chemie. Angew. Chem. Weinheim Bergstr. Ger. 1995, 107 (20), 2476-2479. doi: 10.1002/ange.19951072036.
  31. Burbaum, J. J.; Ohlmeyer, M. H.; Reader, J. C.; Henderson, I.; Dillard, L. W.; Li, G.; Randle, T. L.; Sigal, N. H.; Chelsky, D.; Baldwin, J. J. A Paradigm for Drug Discovery Employing Encoded Combinatorial Libraries. Proc. Natl. Acad. Sci. U. S. A. 1995, 92 (13), 6027-6031. doi: 10.1073/pnas.92.13.6027.
  32. Karnbrock W., Deeg M., Gerhardt J., Rapp W. Solid phase synthesis of hydantoins by thermal cyclization and screening of reaction conditions using APOS 1200. Molecular Diversity, 1998, 4 (3), 165-171. doi: 10.1023/a:1009659303984
  33. Rapp W., Nicholson G., Maier M., Schlotterbeck G., Pursch M., Albert K. Miniaturization in chemistry: Chemical possibilities and physiochemical properties of polymeric microwavesreactors in Innovations and Perspectives in Solid Phase Synthesis & Combinatorial Libraries, Proceedings of the 4th International Symposium 1993, (Epton R., Ed.), Mayflower Scientific Limited, Birmingham, 1996, 97.
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