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TentaGel® MB COOH

€ 77,00*

SIZE
140 - 170 µm
Capacity
0.3 - 0.6 mmol/g
Product number
 MB160003.1G

Product information

TentaGel® resins are grafted copolymers consisting of a low crosslinked polystyrene matrix on which polyethylene glycol (PEG or POE) is grafted via an ethyl ether group which increases stability towards acid treatment and minimizes PEG-leaching. The graft copolymer shows modified physicochemical properties which are highly dominated by the PEG moiety (and no longer by the polystyrene matrix) and has hydrophobic and hydrophilic properties. These copolymers are pressure stable and can be used in batch processes as well as under continuous flow conditions. The PEG spacer is in the range of MW 3000 Da. TentaGel® resins have high diffusion rates and excellent swelling in a wide range of solvents from e.g. toluene to water.
TentaGel® Macrobeads are highlighted by extraordinary large particle diameters and high capacities based on the TentaGel® technology and designed for single bead synthesis and single bead analysis.
TentaGel® amine Macrobeads acylated with succinic acid.
The resin can be used for the immobilization of alcohols by esterification. Cleavage is usually effected by hydrolysis, hydrazinolysis or reduction with LiBH4.

Literature

L 3 Macro Beads

  1. Rapp W., Macrobeads as Microreactors: New Solid-Phase Synthesis Methology in Combinatorial Chemistry, Synthesis and Application, (Wilson S. R., Czarnik A. W., Eds.), John Wiley & Sons, Inc., (1997), 65.
  2. Pursch M., Schlotterbeck G., Tseng L. H., Albert K., Rapp W., Monitoring the reaction progress in combinatorial chemistry: 1H MAS NMR investigations on single macro beads in the suspended state. Angew. Chem. Int. Ed. Engl.1996, 35, 2867-2869. doi: 10.1002/anie.199628671.
  3. Rapp W., Nicholson G., Maier M., Schlotterbeck G., Pursch M., Albert K. Miniaturization in Chemistry: Chemical Possibilities and Physicochemical Properties of Polymeric Microreactors, 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), 97-100

L 4 TentaGel® Overview

  1. Bayer E., Rapp W. New polymer supports for solid-liquid-phase peptide synthesis in Chemistry of Peptides and Proteins, (Voelter W., Bayer E., Ovchinnikov Y. A., Ivanov V.T., Eds.) Walter de Gruyter & Co., Berlin. New York, (1986), 3.
  2. Bayer E., Rapp W., Dtsch. Offen. DE 3,500,180, 10. Juli 1986, Anm. 4. Jan 1985, C.A. 106, 50859.
  3. Bayer, E. Towards the Chemical Synthesis of Proteins. Angew. Chem. Int. Ed. Engl. 1991, 30 (2), 113-129. doi: 10.1002/anie.199101133.
  4. Bayer E., Rapp W., Polystyrene-Immobilized PEG Chains in Poly(Ethylene Glycol) Chemistry: Biotechnical and Biomedical Application, (Harris M., Ed.) Plenum Press New York, (1992), 325.
  5. Bayer E., Rapp W., German Pat. DOS 3714258, 1988.
  6. Bayer, E.; Dengler, M.; Hemmasi, B. Peptide Synthesis on the New Polyoxyethylene-Polystyrene Graft Copolymer, Synthesis of Insulin B 21-30. Int. J. Pept. Protein Res. 1985, 25 (2), 178-186. doi: 10.1111/j.1399-3011.1985.tb02162.x.
  7. Bayer E., Hellstern H., Eckstein H., Synthesis of Immobilized Peptide Fragments on Polystyrene-Polyoxy-ethylene for Affinity Chromatography. Z. Naturforsch. 1987; 42c, 455-460. doi: 10.1515_znc-1987-0422
  8. Rapp W., Zhang L., Häbich R., Bayer E. Polystyrene-Polyoxyethylene graftcopolymers for high speed peptide synthesis in Peptides 1988, Proceedings of the 20th European Peptide Symposium (Jung G., Bayer E., Eds.), Walter de Gruyter, Berlin, (1989), 199.
  9. Zhang L., Rapp W., Bayer E. Scale-up continuous-flow peptide synthesis of a partial sequence of tyrosine kinase using tentacle polymers in Peptides 1992, Proceedings of the22nd European Peptide Symposium (Schneider C. H., Eberle A. N., Eds.), Escom Leiden, (1993), 432.
  10. Karnbrock, W.; Deeg, M.; Gerhardt, J.; Rapp, W. Solid Phase Synthesis of Hydantoins by Thermalcyclization and Screening of Reaction Conditions Using APOS 1200. Mol. Diver. 1998, 4, 165-171. doi: 10.1023/A:1009659303984

L 5 TentaGel® Kinetics

  1. Bayer, E.; Albert, K.; Willisch, H.; Rapp, W.; Hemmasi, B. Carbon-13 NMR Relaxation Times of a Tripeptide Methyl Ester and Its Polymer-Bound Analogs. Macromolecules 1990, 23 (7), 1937-1940. doi: 10.1021/ma00209a010.
  2. Rudinger J., Buetzer P. in Peptides 1974 (Wolman J., Ed.), Wiley, New York, (1975), 211.
  3. Bayer E., Rapp W. Polystyrene-Immobilized PEG Chains Dynamics and Applications in Poly(Ethylene Glycol) Chemistry: Biotechnical and Biomedical Application, (Harris M., Ed.) Plenum Press, New York, (1992), 325.
  4. Zhang L., Rapp W., Bayer E. Continuous flow peptide synthesis: Dependence of the kinetics upon the nature of polymeric support, method of activation and reaction conditions in Peptides 1990, Proceedings of the 21st European Peptide Symposium (Giralt E., Andreus D., Eds.) Escom Leiden, (1991), 196.
  5. Rapp W. Prevention of side reactions by high speed continuous flow peptide synthesis in Peptides 1992, Proceedings of the 22th European Peptide Symposium (Schneider C. H., Eberle A.N., Eds.) Escom Leiden, (1993), 243.
  6. Shemyakin, M. M.; Ovchinnikov, Y. A.; Kinyushkin, A. A.; Kozhevnikova, I. V. Synthesis of Peptides in Solution on a Polymeric Support I. Synthesis of Glycylglycyl-l-Leucylglycine. Tetrahedron Lett. 1965, 6 (27), 2323-2327. doi: 10.1016/s0040-4039(00)70379-0.
  7. Andreatta, R. H.; Rink, H. Zur Problematik der Peptidsynthese an Trägern: Beitrag eines neuen Verfahrens mit löslichen Trägern. Helv. Chim. Acta 1973, 56 (4), 1205-1218. doi: 10.1002/hlca.19730560405.

L 6 TentaGel® Compatibility Water / org. Solvents

  1. Rapp W., Zhang L., Bannwarth W., Bayer E. Biotinylation and phosphorylation of peptides using polyethyleneglycol grafted resins as solid supports in CFPS in Peptides 1992, Proceedings of the 22th European Peptide Symposium, Escom Leiden, (1993), 347.

L 7 TentaGel® and NMR spectroscopy

  1. Look, G. C.; Holmes, C. P.; Chinn, J. P.; Gallop, M. A. Methods for Combinatorial Organic Synthesis: The Use of Fast 13C NMR Analysis for Gel Phase Reaction Monitoring. J. Org. Chem. 1994, 59 (25), 7588-7590. doi: 10.1021/jo00104a010.
  2. Fitch, W. L.; Detre, G.; Holmes, C. P.; Shoolery, J. N.; Keifer, P. A. High-Resolution 1H NMR in Solid-Phase Organic Synthesis. J. Org. Chem. 1994, 59 (26), 7955-7956. doi: 10.1021/jo00105a006.
  3. Keifer, P. A. Influence of Resin Structure, Tether Length, and Solvent upon the High-Resolution 1H NMR Spectra of Solid-Phase-Synthesis Resins. J. Org. Chem. 1996, 61 (5), 1558-1559. doi: 10.1021/jo952001t.
  4. Pursch M., Schlotterbeck G., Tseng L. H., Albert K., Rapp W., Monitoring the reaction progress in combinatorial chemistry: 1H MAS NMR investigations on single macro beads in the suspended state. Angew. Chem. Int. Ed. Engl.1996, 35, 2867-2869. doi: 10.1002/anie.199628671.
  5. 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.

L 11 TentaGel® COOH Resins

  1. Rapp, W.; et al. Continuous flow peptide synthesis on PSPOE-graft-copolymers in Innovation & Perspectives in Solid Phase Synthesis, 1st International Symposium; Ed, R. E., Ed.; SPCC UK Ltd, Birmingham, 1990, 205.
  2. Zhang L. et al., Continuous flow peptide synthesis: Dependence of the kinetics upon the nature of polymeric support, method of activation and reaction conditions in Peptides 1990, Proc. 21st European Peptide Symposium, (Giralt E., Andreu D., Eds.), ESCOM, Leiden, 1990, 196.
  3. Bayer, E. Towards the Chemical Synthesis of Proteins. Angew. Chem. Int. Ed. Engl. 1991, 30 (2), 113-129. doi: 10.1002/anie.199101133.
  4. Routledge, A.; Abell, C.; Balasubramanian, S. An Investigation into Solid-Phase Radical Chemistry - Synthesis of Furan Rings. Synlett 1997, 1 (01), 61-62. doi: 10.1055/s-1997-704.

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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