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
Chemistry(all)
Biochemistry
Colloid and Surface Chemistry

Access to Document

10.1021/ja00855a044

Cite this

@article{4d425ff4355c43afa73b4c413bdf57a9,

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.",

author = "Jiang, {Victor W.} and Krohn, {Kenneth A.} and Welch, {Michael J.}",

year = "1975",

month = oct,

day = "1",

doi = "10.1021/ja00855a044",

language = "English (US)",

volume = "97",

pages = "6551--6556",

journal = "Journal of the American Chemical Society",

issn = "0002-7863",

publisher = "American Chemical Society",

number = "22",

}

TY - JOUR

T1 - Intramolecular Effects of Radioiodine Decay in o-Iodophenol, a Model for Radioiodinated Proteins

AU - Jiang, Victor W.

AU - Krohn, Kenneth A.

AU - Welch, Michael J.

PY - 1975/10/1

Y1 - 1975/10/1

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.

UR - http://www.scopus.com/inward/record.url?scp=0016864484&partnerID=8YFLogxK

UR - http://www.scopus.com/inward/citedby.url?scp=0016864484&partnerID=8YFLogxK

U2 - 10.1021/ja00855a044

DO - 10.1021/ja00855a044

M3 - Article

C2 - 1184870

AN - SCOPUS:0016864484

SN - 0002-7863

VL - 97

SP - 6551

EP - 6556

JO - Journal of the American Chemical Society

JF - Journal of the American Chemical Society

IS - 22

ER -

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

Abstract

ASJC Scopus subject areas

Access to Document

Other files and links

Fingerprint

Cite this