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Fmoc-Cys(StBu) Wang Resin LL

€ 115,00*

SIZE
100 - 200 mesh
Capacity
0.2 - 0.35 mmol/g
Product number
 HLL0751501309.1G

Product information

Wang resins are the standard supports for the synthesis of peptide acids by solid phase synthesis using the Fmoc strategy.
Fmoc protected amino acids are linked to Polystyrene-PHB (Wang resin, consisting of 1% crosslinked polystyrene functionalized with the TFA labile p-benzyloxybenzyl alcohol linker).
50 - 95% TFA treatment generates free peptide acids.
Low loaded Fmoc AA Wang resin - an ideal support for the synthesis of long or difficult peptides.
Capacity: 0.2 - 0.35 mmol/g
Enantiomeric purity*: > 99.5%
Dipeptide content: < 0.5%
*with exception of Cys and His

Fmoc D-amino acids on request.

Literature

L 39 Wang Resin

  1. Wang, S.-S. P-Alkoxybenzyl Alcohol Resin Andp-Alkoxybenzyloxycarbonylhydrazide Resin for Solid Phase Synthesis of Protected Peptide Fragments. J. Am. Chem. Soc. 1973, 95 (4), 1328-1333. doi: 10.1021/ja00785a602.
  2. Lu, G.-S.; Mojsov, S.; Tam, J. P.; Merrifield, R. B. Improved Synthesis of 4-Alkoxybenzyl Alcohol Resin. J. Org. Chem. 1981, 46 (17), 3433-3436. doi: 10.1021/jo00330a009.
  3. Hamper, B. C.; Dukesherer, D. R.; South, M. S. Solid-Phase Synthesis of Proline Analogs via a Three Component 1,3-Dipolar Cycloaddition. Tetrahedron Lett. 1996, 37 (21), 3671-3674. doi: 10.1016/0040-4039(96)00659-4.
  4. Zhang, C.; Moran, E. J.; Woiwode, T. F.; Short, K. M.; Mjalli, A. M. M. Synthesis of Tetrasubstituted Imidazoles via α-(N-Acyl-N-Alkylamino)-β-Ketoamides on Wang Resin. Tetrahedron Lett. 1996, 37 (6), 751-754. doi: 10.1016/0040-4039(95)02310-0.
  5. Wang, Y.; Wilson, S. R. Solid Phase Synthesis of 2,3-Dihydro-4-Pyridones: Reaction of Danishefsky’s Diene with Polymer-Bound Imines. Tetrahedron Lett. 1997, 38 (23), 4021-4024. doi: 10.1016/s0040-4039(97)00824-1.
  6. 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.
  7. Hanessian, S.; Hoan Khai, H. Solution and Solid Phase P-Alkoxybenzylation of Alcohols under Neutral Conditions. Tetrahedron Lett. 1999, 40 (4), 671-674. doi: 10.1016/s0040-4039(98)02531-3.

L 42 Polystyrene-PHB - AA Fmoc Resins

  1. Wang, S. S. Solid Phase Synthesis of Protected Peptides via Photolytic Cleavage of the Alpha-Methylphenacyl Ester Anchoring Linkage. J. Org. Chem. 1976, 41 (20), 3258-3261. doi: 10.1021/jo00882a010.
  2. Lu, G.-S.; Mojsov, S.; Tam, J. P.; Merrifield, R. B. Improved Synthesis of 4-Alkoxybenzyl Alcohol Resin. J. Org. Chem. 1981, 46 (17), 3433-3436. doi: 10.1021/jo00330a009.
  3. Sieber, P. An Improved Method for Anchoring of 9-Fluorenylmethoxycarbonyl-Amino Acids to 4-Alkoxybenzyl Alcohol Resins. Tetrahedron Lett. 1987, 28 (49), 6147-6150. doi: 10.1016/s0040-4039(00)61832-4.

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.

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.
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