• Title/Summary/Keyword: iodination

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Difference in Susceptibility of Tyrosine Residue to Oxidative Iodination between a Thioredoxin Box Region and a Hormonogenic Region

  • Sok, Dai-Eun;Charles J.Sih
    • Archives of Pharmacal Research
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    • v.24 no.5
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    • pp.446-454
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    • 2001
  • Peptide fragments, isolated from proteolytic cleavage of thyroglobulin at specific sites, were examined for the iodination of tyrosine residues. The 50 kDa polypeptide, which was prepared from digestion of bovine thyroglobulin and continuous preparative SDS-PAGE, was subjected to reduction with DTT and alkylation with iodoacetic acid to generate S-car-boxymethylated peptide derivative, which was further hydrohysed by endoproteinase-Asp-N. Peptide products were separated by RP-HPLC, and each fraction was analyzed by LC/ESI-MS and MALDI-MS analyses. Based on the specificity of endoproteinase-Asp-N andthe mass spectra data, a peptide fragment turned out to correspond to a peptide, DALCCVKCPEGSYFQ (1438-1452), characterized by the presence of a thioredoxin box (CVKC) and a tyrosine residue. In addition, another peptide fragment (1453-1465) containing a thioredoxin box (CIPC) and a tyrosine residue was also observed. However, any evidence of iodination of the tyrosine residue present in these peptides was not provided. Meanwhile, tyrosine residues in the peptides, DVEEALAGKYLAGRFA (1366-1381) and DYSGLLLAFQVFLL (1290-1303) were found to be iodinated; mono- or diiodinated tyrosine residues, characteristic of a hormogenic site, existed in both peptides. In addition, the tyrosine residue in the peptide (1218-1252), corresponding to a hormonogenic site was also iodinated. Thus, there was a sharp difference of the susceptibility to oxidative iodination between the tyrosine residue in a hormonogenic site and that in a thioredoxin region. From these results, it is suggested that polypeptide region adjacent to tyrosine residues may govern the susceptibility of tyrosine to oxidative iodination.

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A Direct Transformation of Aryl Aldehydes to Benzyl Iodides Via Reductive Iodination

  • Ruso, Jayaraman Sembian;Rajendiran, Nagappan;Kumaran, Rajendran Senthil
    • Journal of the Korean Chemical Society
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    • v.58 no.1
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    • pp.39-43
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    • 2014
  • A facile transformation of aryl aldehydes to benzyl iodides through one-pot reductive iodination is reported. This protocol displays remarkable functional group tolerance and the title compound was obtained in good to excellent yield.

Radio iodination (II) Radio iodination of various aromatic derivatives in organic solvent at low temperature (放射性 요오드化 反應 (第 II 報) 有機容媒 中에서의 各種 芳香誘導體의 低溫 요오드化 反應)

  • Kim, You-Sun;Kim, Chong-Doo
    • Journal of the Korean Chemical Society
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    • v.12 no.1
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    • pp.35-38
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    • 1968
  • Radio iodination of various aromatic derivatives (aniline, toluene, iodobenzene, acetanilide, benzene, benzoic acid) were achieved at low temperature by a chloroamine-T procedures in presence of polar solvent(dioxane). Organic base (piperidine) was used as the catalyst. Iodine replacement reaction had occured on the aromatic or alicyclic ring by this reaction, and the kind and ratio of iodinated products were proved to be different from those of usual iodide reaction in organic solvent at low temperature. The reactivity of various aromatic or alicyclic compounds towards the present iodination system was evaluated and the scope and limitation of the present procedures in the preparation of radio pharmaceuticals were discussed.

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Novel synthetic method for the preparation of α-iododaphnetin using benzyltrimethylammonium dichloroiodate

  • Kim, Taek-Soo;Kim, Bo-Ram;Park, Jeong Hoon;Yang, Seung Dae
    • Journal of Radiopharmaceuticals and Molecular Probes
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    • v.2 no.1
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    • pp.56-60
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    • 2016
  • Benzyltrimethylammonium dichloroiodate in the presence of $ZnCl_2$ has been used for aromatic iodination of electron rich aromatic compounds. However, Baylis-Hillman type regioselective ${\alpha}$-iodination was carried out electronically rich coumarin compound under mild reaction condition with excellent chemical yield. Finally, $BBr_3$ demethylation gave ${\alpha}$-iododaphnetin.

A Green Protocol for the Bromination and Iodination of the Aromatic Compounds using H5IO6/NaBr and H5IO6/NaI in the Water

  • Yousefi-Seyf, Jaber;Tajeian, Kazem;Kolvari, Eskandar;Koukabi, Nadiya;Khazaei, Ardeshir;Zolfigol, Mohammad Ali
    • Bulletin of the Korean Chemical Society
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    • v.33 no.8
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    • pp.2619-2622
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    • 2012
  • Bromination and iodination of the aromatic compounds have efficiently been carried out at room temperature and $70^{\circ}C$, respectively, in short reaction times using orthoperiodic acid/sodium bromide (1:2) and orthoperiodic acid/sodium iodide (1:2) in water to prepare the corresponding halo compounds with excellent yields.

The Oxidative Iodination of Pyrimidine Bases and their Nucleosides using Iodine/Dimethylformamide/m-Chloroperbenzoic Acid

  • Hwang, Chang-Ho;Park, Jung-Sup;Won, Jeong-Hee;Kim, Jae-Nyoung;Ryu, Eung K.
    • Archives of Pharmacal Research
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    • v.15 no.1
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    • pp.69-72
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    • 1992
  • Pyrimidine bases and their mucleosides were oxidatively iodinated at C-5 position by the reaction of iodine in DMF (dimethylformamide) with MCPBA (m-chloroperbenzoic acid) under mild conditions. For uracil derivatives such as uracil 1a. 1, 3-dimethyluracil 1b, uridine 1c, and 2'-deoxyuridine 1d, the corresponding 5-iodo derivatives were obtained in high yields (71-95%). The iodination of cytidine 3a and 2'-deoxycytidine 3b was achieved in moderate yields (41-56%).

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Synthesis of (S)-5-iodo-2-aminoindan.HCI ((S)-5-요오드 -2-아미노인단.염산염의 합성)

  • 마은숙
    • YAKHAK HOEJI
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    • v.45 no.6
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    • pp.582-587
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    • 2001
  • (S)-5-iodo-2-aminoindan.HCI (7) was synthesized for developing a serotonergic agent. (S)- Phenylalanine was protected with trifuoroacetyl group and compound 2 was prepared by direct iodination in acetic acid and in the presence of I$_2$, KIO$_4$, and sulfuric acid. Compound 3 was cyclized by Friedel-Crafts reaction and reduced with NaBH$_4$ to form 5-iodo-2-(N-trifluoroacetyl)aminoindan-1-ol (4) . This compound was reduced to indan derivative 5 using the triethylsilane and BF$_3$ . Et$_2$O. It was basified with $K_2$CO$_3$ solution and treated with saturated HCl in ethyl ether to isolate compound 7.

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Chemoselective Iodination of Alcohols with CeCl3·7H2O/NaI over SiO2 under Microwave Irradiation

  • Hosseinzadeh, Rahman;Tajbakhsh, Mahmood;Lasemi, Zahra;Sharifi, Ali
    • Bulletin of the Korean Chemical Society
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    • v.25 no.8
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    • pp.1143-1146
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    • 2004
  • A simple and effective procedure for conversion of primary, secondary, allylic and benzylic alcohols into the corresponding iodides is described using $CeCl_3{\cdot}7H_2O/NaI\;over\;SiO_2$ under microwave irradiation. Benzylic alcohols are selectively converted in the presence of saturated alcohols into their corresponding benzylic iodides under these conditions.

A facile synthesis of 4-cyano-3,5-difluorophenol (4-cyano-3,5-difluorophenol의 새로운 합성법)

  • Song, Jeong-Sup
    • Journal of the Korea Academia-Industrial cooperation Society
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    • v.7 no.6
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    • pp.1308-1312
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    • 2006
  • 4-Cyano-3,5-difluorophenol, useful as intermediate in the manufacturing of liquid crystals, was prepared by the regioselective iodination of 3,5-difluorophenol to give 4-iodo-3,5-difluorophenol, which was then converted to 4-cyano-3,5-difluorophenol under a mild reaction condition. The reaction products were characterized by spectroscopic methods and confirmed by comparison of these analytical data with reported values in the literatures.

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