Intramolecular Effects of Radioiodine Decay in o-Iodophenol, a Model for Radioiodinated Proteins

Victor W. Jiang; Kenneth A. Krohn; Michael J. Welch

doi:10.1021/ja00855a044

Intramolecular Effects of Radioiodine Decay in o-Iodophenol, a Model for Radioiodinated Proteins

Victor W. Jiang, Kenneth A. Krohn, Michael J. Welch

Research output: Contribution to journal › Article › peer-review

4 Scopus citations

Abstract

As a model for the chemical effects of the decay of radioiodine in iodinated proteins, [¹³¹I-¹⁴C]-o-iodophenol has been synthesized and the iodine-131 allowed to decay in aqueous solutions containing various phenolic additives. Reference samples were also studied in which the radioiodine was added as ¹³¹I^- to [¹²⁷I-¹⁴C]-o-iodophenol. Similar products were observed from hydrolytic deiodination of the o-iodophenol, radiolysis of the molecule by external radiation, and as a result of decay of organically bound iodine-131. A mechanism is proposed in which decay of the iodine in [¹³¹I-¹⁴C]-o-iodophenol leaves a carbonium ion [C₆H₄(OH)⁺] which in solution reacts to form catechol. It is postulated that the other products formed are oxidation products of catechol.

Original language	English (US)
Pages (from-to)	6551-6556
Number of pages	6
Journal	Journal of the American Chemical Society
Volume	97
Issue number	22
DOIs	https://doi.org/10.1021/ja00855a044
State	Published - Oct 1 1975
Externally published	Yes

ASJC Scopus subject areas

Catalysis
General Chemistry
Biochemistry
Colloid and Surface Chemistry

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title = "Intramolecular Effects of Radioiodine Decay in o-Iodophenol, a Model for Radioiodinated Proteins",

abstract = "As a model for the chemical effects of the decay of radioiodine in iodinated proteins, [131I-14C]-o-iodophenol has been synthesized and the iodine-131 allowed to decay in aqueous solutions containing various phenolic additives. Reference samples were also studied in which the radioiodine was added as 131I- to [127I-14C]-o-iodophenol. Similar products were observed from hydrolytic deiodination of the o-iodophenol, radiolysis of the molecule by external radiation, and as a result of decay of organically bound iodine-131. A mechanism is proposed in which decay of the iodine in [131I-14C]-o-iodophenol leaves a carbonium ion [C6H4(OH)+] which in solution reacts to form catechol. It is postulated that the other products formed are oxidation products of catechol.",

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AU - Jiang, Victor W.

AU - Krohn, Kenneth A.

AU - Welch, Michael J.

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N2 - As a model for the chemical effects of the decay of radioiodine in iodinated proteins, [131I-14C]-o-iodophenol has been synthesized and the iodine-131 allowed to decay in aqueous solutions containing various phenolic additives. Reference samples were also studied in which the radioiodine was added as 131I- to [127I-14C]-o-iodophenol. Similar products were observed from hydrolytic deiodination of the o-iodophenol, radiolysis of the molecule by external radiation, and as a result of decay of organically bound iodine-131. A mechanism is proposed in which decay of the iodine in [131I-14C]-o-iodophenol leaves a carbonium ion [C6H4(OH)+] which in solution reacts to form catechol. It is postulated that the other products formed are oxidation products of catechol.

AB - As a model for the chemical effects of the decay of radioiodine in iodinated proteins, [131I-14C]-o-iodophenol has been synthesized and the iodine-131 allowed to decay in aqueous solutions containing various phenolic additives. Reference samples were also studied in which the radioiodine was added as 131I- to [127I-14C]-o-iodophenol. Similar products were observed from hydrolytic deiodination of the o-iodophenol, radiolysis of the molecule by external radiation, and as a result of decay of organically bound iodine-131. A mechanism is proposed in which decay of the iodine in [131I-14C]-o-iodophenol leaves a carbonium ion [C6H4(OH)+] which in solution reacts to form catechol. It is postulated that the other products formed are oxidation products of catechol.

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Intramolecular Effects of Radioiodine Decay in o-Iodophenol, a Model for Radioiodinated Proteins

Abstract

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