Synthesis and Characterization of the Selenium Analog of Glutathione Disulfide

Takashi Tamura, T. Oikawa, A. Ohtaka, N. Fujii, N. Esaki, K. Soda

Research output: Contribution to journalArticle

23 Citations (Scopus)

Abstract

We synthesized the selenium analog of glutathione disulfide by a liquid phase method and named it glutaselenone (i.e., γ-L-glutamyl-L-selenocysteinylglycine) diselenide. The selenol of selenocysteine was protected by the p-methoxybenzyl group, which was removed by acidolysis with trifluoroacetic acid in the presence of thioanisol. The overall yield of the final product, glutaselenone diselenide, was about 9% based on the starting compound, Se-(p-methoxybenzyl)-L-selenocysteine. Glutaselenone diselenide showed a broad absorption band between 270 and 400 nm and circular dichroism bands around 270 nm (positive) and 330 nm (negative), which were attributable to diselenide bond.

Original languageEnglish
Pages (from-to)151-154
Number of pages4
JournalAnalytical Biochemistry
Volume208
Issue number1
DOIs
Publication statusPublished - Jan 1993
Externally publishedYes

Fingerprint

Selenocysteine
Glutathione Disulfide
Selenium
Trifluoroacetic Acid
Circular Dichroism
Absorption spectra
Liquids
glutaselenone diselenide
methylphenylsulfide
selenol

ASJC Scopus subject areas

  • Molecular Biology
  • Biophysics
  • Biochemistry

Cite this

Synthesis and Characterization of the Selenium Analog of Glutathione Disulfide. / Tamura, Takashi; Oikawa, T.; Ohtaka, A.; Fujii, N.; Esaki, N.; Soda, K.

In: Analytical Biochemistry, Vol. 208, No. 1, 01.1993, p. 151-154.

Research output: Contribution to journalArticle

Tamura, Takashi ; Oikawa, T. ; Ohtaka, A. ; Fujii, N. ; Esaki, N. ; Soda, K. / Synthesis and Characterization of the Selenium Analog of Glutathione Disulfide. In: Analytical Biochemistry. 1993 ; Vol. 208, No. 1. pp. 151-154.
@article{3410f0ed71604b128c7a006c0d256dfe,
title = "Synthesis and Characterization of the Selenium Analog of Glutathione Disulfide",
abstract = "We synthesized the selenium analog of glutathione disulfide by a liquid phase method and named it glutaselenone (i.e., γ-L-glutamyl-L-selenocysteinylglycine) diselenide. The selenol of selenocysteine was protected by the p-methoxybenzyl group, which was removed by acidolysis with trifluoroacetic acid in the presence of thioanisol. The overall yield of the final product, glutaselenone diselenide, was about 9{\%} based on the starting compound, Se-(p-methoxybenzyl)-L-selenocysteine. Glutaselenone diselenide showed a broad absorption band between 270 and 400 nm and circular dichroism bands around 270 nm (positive) and 330 nm (negative), which were attributable to diselenide bond.",
author = "Takashi Tamura and T. Oikawa and A. Ohtaka and N. Fujii and N. Esaki and K. Soda",
year = "1993",
month = "1",
doi = "10.1006/abio.1993.1021",
language = "English",
volume = "208",
pages = "151--154",
journal = "Analytical Biochemistry",
issn = "0003-2697",
publisher = "Academic Press Inc.",
number = "1",

}

TY - JOUR

T1 - Synthesis and Characterization of the Selenium Analog of Glutathione Disulfide

AU - Tamura, Takashi

AU - Oikawa, T.

AU - Ohtaka, A.

AU - Fujii, N.

AU - Esaki, N.

AU - Soda, K.

PY - 1993/1

Y1 - 1993/1

N2 - We synthesized the selenium analog of glutathione disulfide by a liquid phase method and named it glutaselenone (i.e., γ-L-glutamyl-L-selenocysteinylglycine) diselenide. The selenol of selenocysteine was protected by the p-methoxybenzyl group, which was removed by acidolysis with trifluoroacetic acid in the presence of thioanisol. The overall yield of the final product, glutaselenone diselenide, was about 9% based on the starting compound, Se-(p-methoxybenzyl)-L-selenocysteine. Glutaselenone diselenide showed a broad absorption band between 270 and 400 nm and circular dichroism bands around 270 nm (positive) and 330 nm (negative), which were attributable to diselenide bond.

AB - We synthesized the selenium analog of glutathione disulfide by a liquid phase method and named it glutaselenone (i.e., γ-L-glutamyl-L-selenocysteinylglycine) diselenide. The selenol of selenocysteine was protected by the p-methoxybenzyl group, which was removed by acidolysis with trifluoroacetic acid in the presence of thioanisol. The overall yield of the final product, glutaselenone diselenide, was about 9% based on the starting compound, Se-(p-methoxybenzyl)-L-selenocysteine. Glutaselenone diselenide showed a broad absorption band between 270 and 400 nm and circular dichroism bands around 270 nm (positive) and 330 nm (negative), which were attributable to diselenide bond.

UR - http://www.scopus.com/inward/record.url?scp=0027450708&partnerID=8YFLogxK

UR - http://www.scopus.com/inward/citedby.url?scp=0027450708&partnerID=8YFLogxK

U2 - 10.1006/abio.1993.1021

DO - 10.1006/abio.1993.1021

M3 - Article

C2 - 8434784

AN - SCOPUS:0027450708

VL - 208

SP - 151

EP - 154

JO - Analytical Biochemistry

JF - Analytical Biochemistry

SN - 0003-2697

IS - 1

ER -