Preloaded Resins

 
Vol . 2, No. 4
Unnatural Amino Acids II

The latest Update on New Tools for Drug Discovery
Click here to download PDF version. (688 KB)

 


Introduction / Cyclic Amino Acids / Diamino Acids / ß-Amino Acids and Homo Amino Acids
Alanine Derivatives / Phenylalanine Boronic Acids / Proline and Pyroglutamine Derivatives
Other Amino Acid Building Blocks / Coupling Reagents / Preloaded Resins

Preloaded Resins


Would you like to SAVE TIME and MONEY in your lab?
  • No more tedious attachment of the first amino acid.
  • No more need for monitoring the substitution grade.
  • No more need for monitoring the end-capping.

Using PRELOADED RESINS speeds up your peptide synthesis by starting directly with the automated protocol! Take a look below for more detailed information.


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Fluka offers a comprehensive collection of high quality polystyrene and Tentagel® resins (which are composites of polyethylene oxide grafted to a low cross-linked polystyrene matrix) with Fmoc-amino acids derivatives, pre-attached to the most commonly used linker systems. These resins are used for the synthesis of free and protected peptide acids.

Gel-type polystyrene resins cross-linked with 1% DVB are ideally suited for batchwise peptide synthesis in the most commonly used solvents, e.g. DMF, DCM and NMP.1, 2 The polymer beads show good swelling properties in these solvents, i.e. the polymer matrix contributes only to a small volume of the interior of each resin bead compared to the solvent. This allows for an unhindered, fast contact between the growing peptide chains and dissolved reagents, maximizing diffusion rates. Troublesome interactions of the growing peptide chains are successfully reduced.3,4

Among gel type supports, Tentagel® resins offer the following benefits:5,6

  • Equal distribution of functional groups and homogenicity of binding sites throughout a highly solvated and inert polymer network, ideal for the assembly of large molecules such as peptides
  • Properties of the polymers are highly dominated by those of polyethylene oxide (hydrophilic as well as hydrophobic), which contributes 50-70 % (w:w) of the polymer
  • Improved physico-chemical behaviour resulting in consistent and almost solvent-independent swelling properties
  • Tentagels® are applicable in almost all solvent systems due to their solubility in a broad range of solvents
  • The kinetic behaviour of reactive sites, located at the end of the spacer arms, corresponds with those in solution state
  • Tentagel® resins allow the use of solid phase magic angle spinning MAS 1H-NMR as well as gel-phase 13C-NMR spectroscopic techniques for analysis of resin functionalities and resin-bound molecules. Easy and fast determination of functional groups can be accomplished by IR-spectroscopy, in particular by Fourier transform (FT) techniques on flattened beads

The narrow size distribution of the 90µm Tentagel® S beads together with their excellent pressure stability and the overall high diffusion rates make such resins ideally suited for both batch and continuous-flow peptide synthesis. TFA-labile Wang resin is the standard support for batch synthesis of peptide acids following Fmoc/tBu protection scheme.7,8 The Fmoc-amino acids are coupled to the 4-hydroxymethyl phenoxyacetic acid linkers in such a way that epimerisation and dipeptide formation is minimized. The extraordinary mild cleavage conditions for highly acid-labile 2-chlorotrityl and 4-carboxytrityl resins enable the isolation of fully protected peptide fragments for convergent syntheses and selective side-chain derivatisations.9-11 The large steric impediment of the trityl functionality effectively suppresses diketopiperazine (DKP) formation in the synthesis of prolyl peptides.12 C-terminal Cys- and His-residues are introduced to trityl resins avoiding any racemization, thus resulting in enantiomeric pure products. As the amino acids attached to 2-chlorotrityl resin are N-terminal-free, these resins are ready for the coupling reactions without any deprotecting pre-treatments.

 

REFERENCES:

  1. W. C. Chan and P. D. White (Eds), Fmoc Solid Phase Peptide Synthesis, A Practical Approach, Oxford University Press, New York, NY, 2000.
  2. Meldal, M., in Methods Enzymol., Vol. 289 (Solid-Phase Peptide Synthesis), (G. B. Fields, ed.), Academic Press, San Diego 1997, 83.
  3. Sarin, V. K. et al., J. Am. Chem. Soc., 1984, 106, 7845.
  4. Pugh, K.C., Int. J. Peptide Protein Res., 1992, 40, 208;
  5. Bayer, E., Angew. Chem. 1991, 103, 117.
  6. Rapp, W. et al., in Peptides, Chemistry, Structure and Biology, Proc. 14th Am. Pept. Symp., (P. T. P. Kaumaia, R. S. Hodges, eds), Mayflower, England, 1996, 313, 319, 321.
  7. Wang, S. S., J. Am. Chem. Soc. 1973, 95, 1328.
  8. Guy, C. A., Fields, G. B., in Methods Enzymol., Vol. 289 (Solid-Phase Peptide Synthesis), (G. B. Fields, ed.), Academic Press, San Diego 1997, 29.
  9. Barlos, K. et al., Int. J. Pept. Protein Res. 1991, 37, 513.
  10. E. Bayer et al. in Peptides, Chemistry, Structure and Biology, Proc. 13th Am. Pept. Symp., (R. S. Hodges, J. A. Smith, eds),ESCOM, Leiden 1994, 156.
  11. Bollhagen, R. et al., J. Chem. Soc, Chem. Commun., 1994, 2559.
  12. G. Gr|bler et al. in Innovations and Perspectives in Solid Phase Synthesis,3rd International Symposium (R. Epton, ed.), Mayflower Worldwide, Birmingham 1994, 517.

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  Wang resin 2-chlorotrityl-resin, 4-carboxytrityl-resin
Strategy Fmoc Fmoc
Cleavage 95 % TFA
  1. HOAc/TFE /DCM (1:1:8; v:v:v)
  2. HFIP/DCM (1:4; v:v)
  3. 3. 0,5 % TFA/DCM (v:v)
Target Free peptide acids Fully protected peptide acids

ABBREVIATIONS:

DMF (dimethylformamide)
DCM (dichloromethane)
NMP (N-methylpyrrolidone)
TFA (trifluoroacetic acid)
HFI (hexafluoroisopropanol)
DVB (divinylbenzene)
PS (polystyrene)
Trt (trityl)
TFE (trifluoroethanol)