Journal of Organic Chemistry p. 3003 - 3008 (1993)
Update date:2022-08-10
Topics:
Shih, Hsiencheng
N-Halosuccinimides have been found to convert cysteine, S-(acetamidomethyl)-, S-(p-methoxybenzyl)-, or S-(p-methylbenzyl)cysteine into cystine.N-Iodosuccinimide, the mildest reagent among N-halosuccinimides, is applied successfully in the synthesis of (Arg8)-vasopressin and oxytocin by a fully automated process of solid-phase peptide synthesis or by cyclizing the released thiol peptides in DMF-CH2Cl2.These simple and synthetically useful methods have led to the fully automated solid-phase synthesis of (Cys5,Cys12)human growth hormone releasing factor (1-29)-NH2 and apamin based on the combined process of stepwise addition of Boc-amino acids and controlled stepwise formation of the disulfide bonds.These new approaches may be useful in the synthesis of larger and more complex cystine peptides.
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