Carbodiimide-mediated O-sulfation of hydroxy-amino acids and peptides: a reaction suitable for radiolabeling
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 degrees 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. Radiolabeling of peptides by this method can be carried out with a high degree of efficiency if the added (/sup 35/S)sulfuric acid is used carrier free with an acid excess provided by trifluoromethyl sulfonic acid. Under these conditions, over 60% of (/sup 35/S)sulfuric acid was incorporated into insulin and bovine serum albumin. This method may prove useful in the radiolabeling of other peptides and proteins.
- Research Organization:
- Rockefeller Univ., New York, NY
- OSTI ID:
- 5186029
- Journal Information:
- Arch. Biochem. Biophys.; (United States), Vol. 2
- Country of Publication:
- United States
- Language:
- English
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Related Subjects
AMINO ACIDS
LABELLING
LABELLED COMPOUNDS
CHEMICAL PREPARATION
PEPTIDES
ALBUMINS
ELECTROPHORESIS
IMIDES
INSULIN
SULFATES
SULFUR 35
SULFURIC ACID
BETA DECAY RADIOISOTOPES
BETA-MINUS DECAY RADIOISOTOPES
CARBOXYLIC ACIDS
DAYS LIVING RADIOISOTOPES
EVEN-ODD NUCLEI
HORMONES
HYDROGEN COMPOUNDS
INORGANIC ACIDS
ISOTOPES
LIGHT NUCLEI
NUCLEI
ORGANIC ACIDS
ORGANIC COMPOUNDS
ORGANIC NITROGEN COMPOUNDS
OXYGEN COMPOUNDS
PEPTIDE HORMONES
PROTEINS
RADIOISOTOPES
SULFUR COMPOUNDS
SULFUR ISOTOPES
SYNTHESIS
400702* - Radiochemistry & Nuclear Chemistry- Properties of Radioactive Materials