AjiPhase Peptide Synthesis

AjiPhase Peptide Synthesis

Overall Score4.5
  • Generality
  • Reagent Availability
  • Experimental User Friendliness
  • General Characteristics

The advantages of liquid-phase peptide synthesis (LPPS) over solid-phase synthesis (SPPS) include the use of reduced reagents and solvents and the ease of scaling up. The main disadvantage of LPPS is, of course, the difficulty of purification.

The AjiPhase is the LPPS technology developed by Ajinomoto Co. that combines the benefits of LPPS and SPPS.

By using fluorenyl- and diphenylmethyl-type C-terminus anchors containing long alkyl chain(s), post-reaction purification can be done by precipitation (by adding polar solvents).

Ajiphase_2Synthetically challenging peptides (such as hydrophobic peptides) can be accessed more easily with this technology.

  • General References

  • Takahashi, D.; Yamamoto, T. Tetrahedron Lett. 2012, 53, 1936. doi:10.1016/j.tetlet.2012.02.006
  • Takahashi, D.; Inomata, T. J. Pept. Sci. 2012, 18, S35.
  • Takahashi, D.; Yano, T.; Fukui, T. Org. Lett. 2012, 14, 4515. DOI: 10.1021/ol302002g

<Other scalable LPPS>

<General reviews of chemical synthesis of peptides/proteins>

  • Design Principle

The bulky anchor is designed to prevent the peptide from decomposition via diketopiperazine formation (which is the same concept as chlorotrityl solid support). Fluorenyl group has a higher stability in solution than trityl group.

  • External Links

, ,