Utility of Trityl Supports in Fmoc-t-butyl Solid Phase Peptide Synthesis

The utility of the 2-chlorotrityl-chloride supports in Fmoc-t-butyl solid phase synthesis has been widely recognized for its unique properties

CBL was founded on the discovery and development of several key innovations including the trityl resins. CBL is one of the largest global suppliers of peptide synthesis materials, including trityl resins, preloaded trityl resins, Fmoc-amino acids and protected peptide fragments.

A few of these properties include:

 

  • C-Terminal amino acids can be attached in high yields and with minimal racemisation.(1)
  • Minimizes losses from the support occurring during peptide chain elongation.
  • Minimizes diketopiperazine formation at the dipeptide stage.(1,4)
  • Cleavage of peptides from the supports can be effected by mild acid treatment even with fluorinated alcohols. This property provides the option of cleaving fully protected peptides for further fragment condensation.(4)
  • C-Terminal cysteine peptides can be produced without concomitant racemisation with each piperidine treatment.(3)
  • When the methoxytrityl protecting group is used for the side chain of cysteine, it can be removed simultaneously with cleavage from the support offering the prospect of direct disulphide bond formation.(1,2)

 

These versatile supports are readily available in various mesh sizes from CBL either as the basic 2-chlorotrityl chloride polystyrene or with the first amino acid already attached.

 

1. Barlos, K et al. Tetrahedron Letters 30 (1989)3943-3946.

2. Barlos, K et al. (1991) International Journal of Peptide and Protein Research 38, 562-568.

3. R. Steinauer, et al. in “Innovations and perspectives in solid phase synthesis”, R. Epton (Ed.) , Mayflower Scientific Ltd., Birmingham, pp. 689.

4. Bollhagen, R; Schmiedberger, M; Barlos,K, et al. (1994) J. Chem.Soc., Chem. Commun., 22, 2259