Use of 10% sulfuric acid/dioxane for removal of N‐α‐tertiary‐butyloxycarbonyl group during solid phase peptide synthesis Article

HOUGHTEN, RA, BECKMAN, A, OSTRESH, JM. (1986). Use of 10% sulfuric acid/dioxane for removal of N‐α‐tertiary‐butyloxycarbonyl group during solid phase peptide synthesis . 27(6), 653-658. 10.1111/j.1399-3011.1986.tb01061.x

cited authors

  • HOUGHTEN, RA; BECKMAN, A; OSTRESH, JM

authors

abstract

  • The hazards and high costs associated with the use of trifluoroacetic acid (TFA) in the removal of the N‐α‐tertiary‐butyloxycarbonyl (Boc) group during solid phase peptide synthesis prompted an examination of alternative acidolytic reagents for α‐amino group deprotection. N‐α‐Boc‐glycine and N‐α‐Boc‐isoleucine resins as well as an N‐α‐Boc‐peptide resin were used to test the lability to various deprotection mixtures of both the N‐α‐Boc resin group as well as the amino acid or peptide‐O benzyl ester resin linkage. Of the combinations tried, several were found, including 10% H2SO4/dioxane, which gave results roughly comparable to 50% TFA/CH2Cl2. Several peptides, 5–10 amino acid residues in length, have been successfully synthesized using the 10% H2SO4/dioxane mixture and were found to be comparable in purity to the same peptides prepared using the standard TFA/CH2Cl2 method of N‐α‐Boc removal. Thus, for the peptides examined, 10% H2SO4dioxane was found to be an inexpensive, safe, and practical alternative reagent to the more costly and hazardous 50% TFA/CH2Cl2 commonly used in the deprotection step of solid phase peptide synthesis. © 1986 Munksgaard International Publishers Ltd.

publication date

  • January 1, 1986

Digital Object Identifier (DOI)

start page

  • 653

end page

  • 658

volume

  • 27

issue

  • 6