Study on the Effects of 18-Crown-6 in Solid Phase Peptide Synthesis

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Presentation transcript:

Study on the Effects of 18-Crown-6 in Solid Phase Peptide Synthesis

Introduction Fmoc solid phase peptide synthesis produces long peptide chains attached to the same resin that may tangle Tangle limits peptide length and causes a loss of yield Use of Crown Ethers may stabilize intermolecular forces and act as a spacer to prevent tangle

Motivation With the help of crown ethers, it may be easier to synthesize more complicated or otherwise impossible peptides. Use of crown ethers may prevent tangling and increase yield. Crown ethers may reduce the need for expensive protection groups to reduce nucleophilicity of R groups.

Intermolecular Tangle Caused by interactions among polyamide backbone chain. Is the limiting factor that prevents the synthesis of many useful peptides. May be able to be controlled by forcing peptides to interact with another molecule instead of with sibling peptide chains.

Properties of 18-Crown-6 Electron density is directed towards the center of the ring. Capable of hydrogen bonding. Able to ‘thread’ a growing peptide chain. 2-4 Breaks down in the acidic conditions present during the final cleavage step.

Electrostatic Potential map of 18-Crown-6 shows reactive sites in the center of the ring

18-Crown-6 as a Spacer 18-Crown-6 is ‘threaded’ on through intermolecular forces. May reduce interactions with other peptide chains.

Crown Ether Locking If a crown ether is threaded behind a large amino acid, it may become trapped if a second large amino acid is added after it. Trapped ethers can still prevent peptide tangling

Non-Threaded H-Bonding 18-Crown-6 may still hydrogen bond even though it is not threaded.

Crown Ethers at Work in Fmoc Chemistry Threaded crown ethers spread each of the chains apart Non-threaded ethers hydrogen bond with R groups, stabilize charge, and reduce the need for protecting groups.

Conclusions Incorporation of crown ethers may be an affordable way to increase yields and create more exotic peptides. Crown ethers can easily be added to Fmoc protocol

References Merrifield, R.B. J. Am. Chem. Soc. 1963, 85, 2149. Gong, C.; Ji, Q,; Subramaniam, C.; Gibson, H.W. Macromolecules. 1998, 31, 1814. Gong, C.; Gibson, H.W. Macromolecules 1997, 30, 8524. Gong, C.; Glass, T.E.; Gibson, H.W. Macromolecules. 1998, 31, 308.