€ 115,00*
XV18130.012.1G
Product information
A Sophisticated Resin for the Solution of Synthesis Challenges. TentaGel® XV resin (XV stands for "Extended Swelling Volume") is a new member of the TentaGel® family. Modifications on the polystyrene backbone change the swelling properties of the PEG grafted resin. Swelling properties are in the same range or even higher compared to PEGA or Chematrix resins. The polar PEG spacers allow the composite resin to swell in a wide range of solvents including water, methanol, DMF, DCM. Nevertheless, the handling is still very easy and similar to other TentaGel® resins. The high swelling creates an extended reaction space. This enlarged reaction volume meets the requirement for ideal conditions for the synthesis of difficult sequences, aggregating peptides, mini proteins and PNAs in high purities and excellent yields.
Purified yield of PNA4-peptide15-PNA11
Resin yield [%]
Wang resin 0
Chematrix 20
TentaGel® XV 32
This resin is derived from TentaGel® NH2 resin by coupling with the 4-carboxytrityl linker. For further reactions the alcohol group has to be converted to the chloride and then used immediately. This highly acid sensitive linker is useful for the immobilization of alcohols, amines and carboxylic acids. Cleavage is in general achieved by using either 5 - 50% TFA in DCM (containing 5% triisopropylsilane) or acetic acid.
This resin can also be used in Fmoc peptide synthesis. Carboxylic acids can be released under very mild acidic conditions by treatment with AcOH/TFE/DCM or HFIP in DCM. Completely protected peptides are generated under these conditions. Residues which are sensitive to racemisation during esterification reactions like His and Cys can be attached to the resin without racemisation. Due to the bulkiness of the trityl group, diketopiperazine formation is suppressed which makes this linker ideal for peptides with C-terminal Pro.
Literature
L 4 TentaGel® Overview
- 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.
- Bayer E., Rapp W., Dtsch. Offen. DE 3,500,180, 10. Juli 1986, Anm. 4. Jan 1985, C.A. 106, 50859.
- Bayer, E. Towards the Chemical Synthesis of Proteins. Angew. Chem. Int. Ed. Engl. 1991, 30 (2), 113-129. doi: 10.1002/anie.199101133.
- 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.
- Bayer E., Rapp W., German Pat. DOS 3714258, 1988.
- 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.
- 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
- 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.
- 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.
- 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
- 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.
- Rudinger J., Buetzer P. in Peptides 1974 (Wolman J., Ed.), Wiley, New York, (1975), 211.
- 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.
- 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.
- 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.
- 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.
- 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
- 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
- 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.
- 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.
- 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.
- 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.
- 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 14 TentaGel® Trt-OH Resins
- Bayer, E. Towards the Chemical Synthesis of Proteins. Angew. Chem. Int. Ed. Engl. 1991, 30 (2), 113-129. doi: 10.1002/anie.199101133.
- Gayo, L. M.; Suto, M. J. Traceless Linker: Oxidative Activation and Displacement of a Sulfur-Based Linker. Tetrahedron Lett. 1997, 38 (2), 211-214. doi: 10.1016/s0040-4039(96)02256-3.
- Bayer E. et al. New polymer and strategy for the solid-phase synthesis of protected peptide fragments in Peptides. Chemistry, Structure and Biology, Proceedings of the 13th American Peptide Symposium, (Hodges R. S. Smith J. A., Eds.), ESCOM Science Publishers B.V., Leiden, Netherlands, 1994, 156
- Fréchet, J. M. J.; Haque, K. E. Use of Polymers as Protecting Groups in Organic Synthesis. II. Protection of Primary Alcohol Functional Groups. Tetrahedron Lett. 1975, 16 (35), 3055-3056. doi: 10.1016/s0040-4039(00)75071-4.
- Fyles, T. M.; Leznoff, C. C. The use of polymer supports in organic synthesis. V. The preparation of monoacetates of symmetrical diols. Can. J. Chem. 1976, 54 (6), 935-942. doi: 10.1139/v76-135.
- Vliet V. et al.Protected Peptide Intermediates Using a Trityl Linker on a Solid Support in Innovation and Perspectives in Solid Phase Synthesis and Related Technologies 1992: Peptides, Polypeptides and Oligonucleotides; (Epton, R., Ed.); Intercept: Wimborne, UK, 1992, 475.
- Vliet V. et al., Protected peptide intermediates using a trityllinker on a solid support in Peptides 1992, Proc. 22nd European Peptide Symposium, (C. H. Schneider, A. N. Eberle, Eds.), ESCOM, Leiden, 1993, 279.
- Grübler G. et al., Solid Phase Synthesis of a C-terminal Proline Peptide Using an Anchor System Suppressing Diketopiperazine Formation in Innovation & Perspectives in Solid Phase Synthesis, 3rd International Symposium, (Epton R., Ed.), Mayflower Worldwide Ltd., Birmingham, 1994, 517-520.
- Bollhagen, R.; Schmiedberger, M.; Barlos, K.; Grell, E. A New Reagent for the Cleavage of Fully Protected Peptides Synthesised on 2-Chlorotrityl Chloride Resin. J. Chem. Soc. Chem. Commun. 1994, No. 22, 2559. doi: 10.1039/c39940002559.
- Krchňák, V.; Weichsel, A. S. Polymer-Supported Synthesis of Diverse Perhydro-1,4-Diazepine-2,5-Diones. Tetrahedron Lett. 1997, 38 (42), 7299-7302. doi: 10.1016/s0040-4039(97)01772-3.
L 24 Library Overview
- Furka, et al., 10th Int. Symp. Med. Chem., Budapest, 1988.
- 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.
- Furka, et al., 14th Int. Cong. of Biochem., Prague, (1988).
- 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
- 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.
- 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.
- 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.
- 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.
- 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.
- 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.
- 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.
- 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.
- 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.
- 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.
- 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.
- Wennemers, H.; Still, W. C. Peptide Complexation in Water. Tetrahedron Lett. 1994, 35 (35), 6413-6416. doi: 10.1016/s0040-4039(00)78233-5.
- 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.
- 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.
- 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.
- 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.
- 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.
- 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.
- 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.
- 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.
- 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.
- 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.
- 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.
- 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.
- 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.
- 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.
- 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.
- 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.
- 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.
- 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.
- 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.
- 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
- 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 58 TentaGel® XV
- Rapp, W.; et al. Preventing failure in difficult sequences: An improved resin matrix, its properties and application in Peptides 2012: Proceedings of the Thirty-Second European Peptide Symposium, (Eds. G. Kokotos, V. Constantinou-Kokotos, J. Matsoukas), European Peptide Society (2012), 28-29.
- Rawer, S.; et al. Optimization of the PNA-synthesis using different bases for Fmoc-deprotection in Peptides 2012: Proceedings of the Thirty-Second European Peptide Symposium, (Eds. G. Kokotos, V. Constantinou-Kokotos, J. Matsoukas), European Peptide Society (2012), 406-407.
- Pipkorn R, Rawer S, Wiessler M, Waldeck W, Koch M, Schrenk HH, Braun K. SPPS resins impact the PNA-syntheses’ improvement. Int J Med Sci. 2013; 10(3): 331-337. doi:10.7150/ijms.5374
- Synthesis guidelines see "General Information"