Carbodiimide-mediated O-sulfation of hydroxy-amino acids and peptides

A reaction suitable for radiolabeling

Sandor Pongor, Michael Brownlee, Anthony Cerami

Research output: Contribution to journalArticle

4 Citations (Scopus)

Abstract

Carbodiimide-mediated sulfation of hydroxy-amino acids, peptides, and proteins can be accomplished in dry dimethylformamide by incubation in a 20-50 molar excess of sulfuric acid and various concentrations of dicyclohexyl carbodiimide [(1-ethyl-(3-dimethylaminopropyl)carbodiimide or 1-cyclohexyl-3-(2-morpholoethyl)carbodiimide p-toluene sulfonate)] at 4 °C for 2-4 h. Under these conditions, hydroxy-amino acids are quantitatively converted into O-sulfates, while cysteine yields the S-sulfonate. Other amino acids, including tryptophan, do not react and are recovered quantitatively. Porcine sodium insulin yields a product that can be separated into six bands by nondenaturing polyacrylamide gel electrophoresis. Radioloabeling of peptides by this method can be carried out with a high degree of efficiency if the added [35S]sulfuric acid is used carrier free with an acid excess provided by trifluoromethyl sulfonic acid. Under these conditions, over 60% of [35S]sulfuric acid was incorporated into insulin and bovine serum albumin. This method may prove useful in the radiolabeling of other peptides and proteins.

Original languageEnglish (US)
Pages (from-to)458-463
Number of pages6
JournalArchives of Biochemistry and Biophysics
Volume238
Issue number2
DOIs
StatePublished - May 1 1985
Externally publishedYes

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Carbodiimides
Hydroxy Acids
Amino Acids
Amino Acids, Peptides, and Proteins
Insulin, Regular, Pork
Insulin
Dimethylformamide
Peptides
Sulfonic Acids
Bovine Serum Albumin
Electrophoresis
Tryptophan
Sulfates
Cysteine
Polyacrylamide Gel Electrophoresis
Acids
peptide A
sulfuric acid
Proteins

ASJC Scopus subject areas

  • Biochemistry
  • Biophysics
  • Molecular Biology

Cite this

Carbodiimide-mediated O-sulfation of hydroxy-amino acids and peptides : A reaction suitable for radiolabeling. / Pongor, Sandor; Brownlee, Michael; Cerami, Anthony.

In: Archives of Biochemistry and Biophysics, Vol. 238, No. 2, 01.05.1985, p. 458-463.

Research output: Contribution to journalArticle

Pongor, Sandor ; Brownlee, Michael ; Cerami, Anthony. / Carbodiimide-mediated O-sulfation of hydroxy-amino acids and peptides : A reaction suitable for radiolabeling. In: Archives of Biochemistry and Biophysics. 1985 ; Vol. 238, No. 2. pp. 458-463.
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