Abstract
The reagent o-iodosobenzoic acid (IBA)+ has been reported to cleave specifically tryptophanyl peptide bonds in proteins with 70–100% yields (1). However, the results obtained in a number of laboratories (2–4) indicated that the reagent is not as selective as originally reported, since cleavage occurs also at tyrosine in moderate to high yields. Subsequently, Mahoney et al. (5,6) proposed that o-iodoxybenzoic acid thought to be present as a contaminant in the commercially available reagent is responsible for the observed cleavage at tyrosine. The results of the studies reported herein rule out this proposal and show that IBA, under the experimental conditions of protein fragmentation (80% aqueous acetic acid containing 4M Gdn.HCl), mediates the oxidative chlorination of both the indole nucleus of tryptophan and the phenol ring of tyrosine with concomitant peptide bond cleavage++.
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ArticleNote
A more comprehensive report on the fragmentation of peptides and proteins using IBA will be published elsewhere (7).
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Abbreviations
- IBA:
-
o-iodosobenzoic acid
- BNPS-skatole:
-
2-(2-nitrophenylsulfenyl)-3-methyl-3-bromoindolenine
- NBS:
-
N-bromosuccinimide
- DMSO:
-
dimethyl sulfoxide
- Gdn.HCl:
-
guanidine hydrochloride
References
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Fontana, A., Dalzoppo, D., Grandi, C., Zambonin, M. (1982). Protein Fragmentation with o-Iodosobenzoic Acid. In: Elzinga, M. (eds) Methods in Protein Sequence Analysis. Experimental Biology and Medicine, vol 3. Humana Press. https://doi.org/10.1007/978-1-4612-5832-2_27
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DOI: https://doi.org/10.1007/978-1-4612-5832-2_27
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