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Synthesis of insulin-like growth factor I using N-methyl pyrrolidinone as the coupling solvent and trifluoromethane sulphonic acid cleavage from the resin.

International journal of peptide and protein research (1990-10-01)
C J Bagley, K M Otteson, B L May, S N McCurdy, L Pierce, F J Ballard, J C Wallace
ABSTRACT

Insulin-like growth factor I (IGF-I), a protein of 70 amino acid residues and 3 cystine bridges, has been synthesized by two solid phase Boc methods. The first method used N-methylpyrrolidinone as the solvent with single coupling cycles while the second synthesis used dimethylformamide and dichloromethane as the solvents with a double-coupling protocol. In both cases, trifluoroacetic acid/trifluoromethanesulphonic acid cleavage of the peptide from the resin was employed. Purification of the cleavage products followed by removal of the S-acetamidomethyl protecting groups gave reduced peptides which were then oxidized under conditions favouring the formation of the correct disulphide bonds. The purified synthetic IGF-I peptides were full agonists of natural IGF-I in a radioimmunoassay, in an IGF-I radioreceptor assay, in a bioassay which measures the stimulation of protein synthesis in rat L6 myoblasts and in an IGF-binding protein competitive binding assay. Moreover, in each of these assays, the synthetic IGF peptides were found to be at least 70% as potent as natural IGF-I.

MATERIALS
Product Number
Brand
Product Description

Sigma-Aldrich
1-Methyl-2-pyrrolidinone, anhydrous, 99.5%
Sigma-Aldrich
1-Methyl-2-pyrrolidinone, ACS reagent, ≥99.0%
Sigma-Aldrich
1-Methyl-2-pyrrolidinone, ReagentPlus®, 99%
Sigma-Aldrich
1-Methyl-2-pyrrolidinone, suitable for HPLC, ≥99%
Sigma-Aldrich
1-Methyl-2-pyrrolidinone, biotech. grade, ≥99.7%
Supelco
1-Methyl-2-pyrrolidinone, analytical standard