Effective use of free thiols as scavengers for HF cocktails to deprotect bromo- and chloroacetylated synthetic peptides.
A variety of thiol-containing compounds, in combination with m-cresol, were tested as scavengers in hydrogen fluoride (HF) cocktails that are used to deprotect haloacetylated peptidyl resins. Our results indicate that brome and chloroacetyl moieties on a synthetic peptide remain intact following HF treatment when the HF cocktail contains m-cresol along with either thiophenol, m-thiocresol or 1,2-ethanedithiol. The free thiols prevent the formation of a number of impurities in the preparation of bromo- and chloroacetylated peptides that contain amino acids that could be oxidized in a nonreducing HF environment. Ethvimethylsulfide, however, could not be used with bromoacetylated peptides, but it could be used with chloroacetylated peptides.
Ivanov
B B
BB
National Institute of Dental Research, NIH, Bethesda, MD, USA.
Robey
F A
FA
D000107:Acetylation; D000595:Amino Acid Sequence; D002851:Chromatography, High Pressure Liquid; D003408:Cresols / Q000737:chemistry; D015699:HIV Envelope Protein gp120 / Q000737:chemistry*; D006858:Hydrofluoric Acid / Q000737:chemistry*; D008969:Molecular Sequence Data; D010446:Peptide Fragments / Q000138:chemical synthesis* / Q000737:chemistry*; D013438:Sulfhydryl Compounds / Q000737:chemistry*
D003408:Cresols; D015699:HIV Envelope Protein gp120; D010446:Peptide Fragments; D013438:Sulfhydryl Compounds; C042041:3-cresol; D006858:Hydrofluoric Acid