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solid phase peptide synthesis procedure

Author:N/A    | Post time:2012-05-23


The most common resin used the McGarvey lab is the Wang Resin.  This is an inexpensive and versatile resin that is standard for solid phase peptide synthesis.  Here are examples of other resins that have been used in the McGarvey Lab:
Solid Phase Synthesis Set-up

One of the most useful aspects of solid phase synthesis is the ease in which reagents can be removed.  Therefore it is important to have a simple way to remove the reagents and wash the resin.  The method illustrated below is an effective and inexpensive way to run solid phase reactions.

The Mixer - used to agitate reaction without destroying the beads

The Reaction Vessel - as an alternative to glass containers with non-replaceable filters, these empty syringe cartridges can be fit with a filter, a stopcock, and a plastic cap.  These materials are compatible with all the reagents involved with solid phase peptide synthesis and the total cost of any size set-up (up to 50ml) is less than $1.

The Set-up - the resin can be added to the reaction vessel and clamped to the mixer.  An inert gas line can added by inserting a needle through the plastic cap.  The reagents can simply be added and shaken until the reaction is complete.


The Removal of Reagents - a piece of PFA tubing (like tubing used for HPLC) can be attached to the stopcock and a bent vacuum adapter (this can be done by forcing a beveled piece of tubing through a rubber septum).  The adapter is then hooked to a vacuum source and a round bottom.  By opening the stopcock, the solvent, reagents, and subsequent washes can be collected in the round bottom.  The resin is then ready to be dried or taken on to the next reaction.

Resin Loading Procedures

To place the first amino acid on the resin, the symmetrical anhydride method is most often employed.  This involves dissolving 10 eq (relative to the resin loading) of the amine protected amino acid in dry DCM (a few drops of DMF may be added if needed to dissolve the amino acid).  To this solution stirring at 0 , 5 eq of DIC is added and stirred for 20 minutes.  The mixture is then concentrated in vacuo and redissolved in DMF.  The resulting solution is added to the resin and shaken until the reaction is complete (usually 1 h to 5 h  - catalytic DMAP may be added).  The mixture is filtered, rinsed several times with DMF and DCM, and dried.

Standard Coupling Procedures
Addition of Fmoc protected amino acid residues can involve many different activators (such as HBtU, PyBOP, or HATU).  Standard procedures for these coupling reagents are as follows:
The Fmoc amino acid to be added (5 eq) is dissolved in a minimal amount of DMF with PyBOP, HBtU, or HATU (4.9 eq of any one) and HOBt (5 eq for PyBOP or HBtU - 5 eq of HOAt is used for HATU).  DIPEA (10 eq) is added and the solution is added immediately to the free amine resin in the set-up described above.  The reaction is shaken for 30 minutes to 2 h (Kaiser test may be used to determine if the coupling is >95% complete) and drained.  The resin is washed three times with DMF, three times with DCM, and dried in vacuo.

Fmoc Removal Procedure

To remove the terminal Fmoc group, piperidine in DMF is most commonly used.  The standard procedure is as follows:
A fresh solution of 20% piperidine in DMF is added to the resin and shaken for 5 minutes.  The resin is drained, piperidine solution is added agian, and the mixture is shaken for 5 minutes.  The process is completed one more time and the solution is removed.  The resin is washed three times with DMF, three times with DCM, and dried in vacuo.

Cleavage Procedure (acid labile resins)

Removal of the peptide from most acid sensitive resins (such as the Wang resin) involves triflouroacetic acid and an acid scavanger.  The standard procedure is as follows:
To the resin in the previously mentioned reaction vessel, a 10% solution of TES in DCM is added and shaken for 15 minutes.  To this mixture an equal volume of TFA is added and shaken for an additional 1.5 h.  The resin is filtered and washed (DCM:TFA 1:1) twice, collecting the filtrate.  The organic solution is concentrated in vacuo and purified.

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