Which amino acid derivatives can be used for Boc-SPPS?

Mar 16, 2021

The side-chain protecting groups have to withstand repetitive treatment with trifluoroacetic acid in methylene chloride.

Derivatives of trifunctional amino acids for “standard” Boc-SPPS:

  • Boc-Arg(Tos)-OH
  • Boc-Asp(OcHex)-OH
  • Boc-Asn(Xan)-OH
  • Boc-Cys(Mob)-OH, Boc-Cys(MBzl)-OH
  • Boc-Gln(Xan)-OH
  • Boc-Glu(OcHex)-OH
  • Boc-His(Tos)-OH
  • Boc-Lys(2-chloro-Z)-OH
  • Boc-Ser(Bzl)-OH
  • Boc-Thr(Bzl)-OH
  • Boc-Trp-OH, Boc-Trp(For)-OH
  • Boc-Tyr(2-bromo-Bzl)-OH, Boc-Tyr(2,6-dichloro-Bzl)-OH

All lateral protecting groups can be removed with HF (removal of For only in the presence of a thiol).