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H-Nle-2-CT Polystyrene Resin

€ 271,00*

SIZE
200 - 400 mesh
Capacity
0.4 - 1.2 mmol/g
Product number
 H0370753319.5G

Product information

Amino acids linked to Polystyrene-2-chlorotrityl chloride resin.
A very acid sensitive resin suitable for the synthesis of protected peptide fragments by the Fmoc strategy. 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. This resin has also been used in the solid phase synthesis of ß-peptides via the Arndt-Eistert homologation of Fmoc-protected amino acid diazoketones.
Cleavage from this resin is achieved for protected peptides by treatment either with AcOH/trifluoroethanol/DCM or 0.5% TFA in DCM or hexafluoroisopropanol. Free peptides are released with 95% TFA.
Fmoc D-amino acids on request

Literature

L 38 Polystyrene-2-Cl-Trt AA Resins

  1. Barlos, K.; Gatos, D.; Kallitsis, J.; Papaphotiu, G.; Sotiriu, P.; Wenqing, Y.; Schäfer, W. Darstellung geschützter Peptidfragmente unter Einsatz substituierter Triphenylmethyl-Harze. Tetrahedron Lett. 1989, 30 (30), 3943-3946. doi: 10.1016/s0040-4039(00)99290-6.
  2. Barlos, K.; Gatos, D.; Kapolos, S.; Papaphotiu, G.; Schäfer, W.; Wenqing, Y. Veresterung von partiell geschützten Peptidfragmenten mit Harzen. Einsatz von 2-Chlortritylchlorid zur Synthese von Leu15 -gastrin I. Tetrahedron Lett. 1989, 30 (30), 3947-3950. doi: 10.1016/s0040-4039(00)99291-8.
  3. Barlos, K.; Gatos, D.; Schäfer, W. Synthesis of Prothymosinα(ProTα)—a Protein Consisting of 109 Amino Acid Residues. Angew. Chem. Int. Ed. Engl. 1991, 30 (5), 590-593. doi: 10.1002/anie.199105901.
  4. Barlos, K.; Gatos, D.; Papaphotiou, G.; Schäfer, W. Synthese von Calcitonin-Derivaten durch Fragmentkondensation in Lösung und am 2-Chlortrityl-Harz. Liebigs Ann. Chem. 1993, 1993 (3), 215-220. doi: 10.1002/jlac.199319930139.
  5. Barlos, K., Chatzi, O., Gatos, D., Stavropoulos, G. 2-Chlorotrityl chloride resin, Studies on anchoring of Fmoc-amino acids and peptide cleavage. Int. J. Peptide Protein Res. 1991, 37 (6), 513-520. doi: 10.1111/j.1399-3011.1991.tb00769.x
  6. Barlos, K.; Gatos, D.; Kutsogianni, S.; Papaphotiou, G.; Poulos, C.; Tsegenidis, T. Solid Phase Synthesis of Partially Protected and Free Peptides Containing Disulphide Bonds by Simultaneous Cysteine Oxidation-Release from 2-Chlorotrityl Resin. Int. J. Pept. Protein Res. 1991, 38 (6), 562-568. doi: 10.1111/j.1399-3011.1991.tb01540.x.
  7. Barlos, K.; Gatos, D.; Kapolos, S.; Poulos, C.; Schäfer, W.; Yao, W. Q. Application of 2-Chlorotrityl Resin in Solid Phase Synthesis of (Leu15)-Gastrin I and Unsulfated Cholecystokinin Octapeptide. Selective O-Deprotection of Tyrosine. Int. J. Pept. Protein Res. 1991, 38 (6), 555-561. doi: 10.1111/j.1399-3011.1991.tb01539.x.

L 37 Chloro-(2’-chloro)trityl Polystyrene Resins

  1. Barlos, K.; Gatos, D.; Kallitsis, J.; Papaphotiu, G.; Sotiriu, P.; Wenqing, Y.; Schäfer, W. Darstellung geschützter Peptidfragmente unter Einsatz substituierter Triphenylmethyl-Harze. Tetrahedron Lett. 1989, 30 (30), 3943-3946. doi: 10.1016/s0040-4039(00)99290-6.
  2. Barlos, K.; Gatos, D.; Kapolos, S.; Papaphotiu, G.; Schäfer, W.; Wenqing, Y. Veresterung von partiell geschützten Peptidfragmenten mit Harzen. Einsatz von 2-Chlortritylchlorid zur Synthese von Leu15 -gastrin I. Tetrahedron Lett. 1989, 30 (30), 3947-3950. doi: 10.1016/s0040-4039(00)99291-8.
  3. Barlos, K.; Gatos, D.; Schäfer, W. Synthesis of Prothymosinα(ProTα)—a Protein Consisting of 109 Amino Acid Residues. Angew. Chem. Int. Ed. Engl. 1991, 30 (5), 590-593. doi: 10.1002/anie.199105901.
  4. Barlos, K., Chatzi, O., Gatos, D., Stavropoulos, G. 2-Chlorotrityl chloride resin, Studies on anchoring of Fmoc-amino acids and peptide cleavage. Int. J. Peptide Protein Res. 1991, 37 (6), 513-520. doi: 10.1111/j.1399-3011.1991.tb00769.x
  5. Barlos, K.; Gatos, D.; Kutsogianni, S.; Papaphotiou, G.; Poulos, C.; Tsegenidis, T. Solid Phase Synthesis of Partially Protected and Free Peptides Containing Disulphide Bonds by Simultaneous Cysteine Oxidation-Release from 2-Chlorotrityl Resin. Int. J. Pept. Protein Res. 1991, 38 (6), 562-568. doi: 10.1111/j.1399-3011.1991.tb01540.x.
  6. Barlos, K.; Gatos, D.; Kapolos, S.; Poulos, C.; Schäfer, W.; Yao, W. Q. Application of 2-Chlorotrityl Resin in Solid Phase Synthesis of (Leu15)-Gastrin I and Unsulfated Cholecystokinin Octapeptide. Selective O-Deprotection of Tyrosine. Int. J. Pept. Protein Res. 1991, 38 (6), 555-561. doi: 10.1111/j.1399-3011.1991.tb01539.x.
  7. Barlos, K.; Gatos, D.; Papaphotiou, G.; Schäfer, W. Synthese von Calcitonin-Derivaten durch Fragmentkondensation in Lösung und am 2-Chlortrityl-Harz. Liebigs Ann. Chem. 1993, 1993 (3), 215-220. doi: 10.1002/jlac.199319930139.
  8. Egner, B. J.; Cardno, M.; Bradley, M. Linkers for Combinatorial Chemistry and Reaction Analysis Using Solid Phase in Situ Mass Spectrometry. J. Chem. Soc. Chem. Commun. 1995, No. 21, 2163-2164. doi: 10.1039/c39950002163.
  9. Leznoff, C. C. The Use of Insoluble Polymer Supports in General Organic Synthesis. Acc. Chem. Res. 1978, 11 (9), 327-333. doi: 10.1021/ar50129a002.
  10. Nash, I. A.; Bycroft, B. W.; Chan, W. C. Dde - A Selective Primary Amine Protecting Group: A Facile Solid Phase Synthetic Approach to Polyamine Conjugates. Tetrahedron Lett. 1996, 37 (15), 2625-2628. doi: 10.1016/0040-4039(96)00344-9.
  11. Hoekstra, W. J.; Greco, M. N.; Yabut, S. C.; Hulshizer, B. L.; Maryanoff, B. E. Solid-Phase Synthesis via N-Terminal Attachment to the 2-Chlorotrityl Resin. Tetrahedron Lett. 1997, 38 (15), 2629-2632. doi: 10.1016/s0040-4039(97)00447-4.
  12. Akaji, K.; Kiso, Y. Macrocyclization on Solid Support Using Heck Reaction. Tetrahedron Lett. 1997, 38 (29), 5185-5188. doi: 10.1016/s0040-4039(97)01123-4.
  13. Marti, R. E.; Bleicher, K. H.; Bair, K. W. Solid Phase Synthesis of β-Peptides via Arndt-Eistert Homologation of Fmoc-Protected Amino Acid Diazoketones. Tetrahedron Lett. 1997, 38 (35), 6145-6148. doi: 10.1016/s0040-4039(97)01420-2.
  14. 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.
  15. Fujiwara, Y.; Akaji, K.; Y Kiso, Y. Racemization-Free Synthesis of C-Terminal Cysteine-Peptide Using 2-Chlorotrityl Resin. Chem. Pharm. Bull. 1994, 42 (3), 724-726. doi: 10.1248/cpb.42.724.
  16. McNally, J. J.; Youngman, M. A.; Dax, S. L. Mannich Reactions of Resin-Bound Substrates: 2. A Versatile Three-Component Solid-Phase Organic Synthesis Methodology. Tetrahedron Lett. 1998, 39 (9), 967-970. doi: 10.1016/s0040-4039(97)10716-x.
  17. Shankar, B. B.; Yang, D. Y.; Girton, S.; Ganguly, A. K. One Pot Solid Phase Synthesis of Isoxazolines. Tetrahedron Lett. 1998, 39 (17), 2447-2448. doi: 10.1016/s0040-4039(98)00237-8.

L 26 Polystyrene Resins

  1. Merrifield R. B., Peptide synthesis on a solid polymer, Fed. Proc. Fed. Amer. Soc. Exp. Biol., 1962, 21, 412.
  2. Merrifield, R. B. Solid Phase Peptide Synthesis. I. the Synthesis of a Tetrapeptide. J. Am. Chem. Soc. 1963, 85 (14), 2149-2154. doi: 10.1021/ja00897a025.
  3. Marshall G. R., Merrifield R. B., in Biochemical Aspects of Reactions on Solid Supports, (Stark G., Ed.), Academic Press, N.Y. 1971.
  4. Barany, G., Merrifield, R.B. Solid phase peptide synthesis in The Peptides. Vol. 2, (Gross, E., Meienhofer, J., Eds.), Academic Press. New York, 1979, 2.
  5. Gordon, E. M.; Barrett, R. W.; Dower, W. J.; Fodor, S. P.; Gallop, M. A. Applications of Combinatorial Technologies to Drug Discovery. 2. Combinatorial Organic Synthesis, Library Screening Strategies, and Future Directions. J. Med. Chem. 1994, 37 (10), 1385-1401. doi: 10.1021/jm00036a001.
  6. Gallop, M. A.; Barrett, R. W.; Dower, W. J.; Fodor, S. P.; Gordon, E. M. Applications of Combinatorial Technologies to Drug Discovery. 1. Background and Peptide Combinatorial Libraries. J. Med. Chem. 1994, 37 (9), 1233-1251. doi: 10.1021/jm00035a001.
  7. Combinatorial Peptide and Nonpeptide Libraries: A Handbook, G. Jung, Ed., Wiley-VCH Verlag: Weinheim, Germany, 1996.
  8. Thompson, L. A.; Ellman, J. A. Synthesis and Applications of Small Molecule Libraries. Chem. Rev. 1996, 96 (1), 555-600. doi: 10.1021/cr9402081.

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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