• Title/Summary/Keyword: 1-hydroxy-2-pyridone

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Synthesis of 4-(2'-(N-(1-methyl-3'-carbamylphenyl)-n-propyl))aminoethyl)-1-hydroxy-2-pyridone (4-(2'-(N-(1-메틸-3-(3'-카바밀페닐)-n-프로필))아미노에틸)-1-히드록시-2- 피리돈의 합성)

  • 윤성화
    • YAKHAK HOEJI
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    • v.37 no.1
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    • pp.36-40
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    • 1993
  • The 4-(2'-(N-(l-methyl-3'-carbamylphenyl)-n-propyl))aminoethyl)-l- hydroxy-2-pyridone which has isoelectronic and isosteric structural similarity with dobutamine without having the Catechol-O- Methyltransferase(COMT) vulnerable m-hydroxy group was synthesized via 12 synthetic steps.

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Application of Bioisosterism in Development of Novel Cardiotonics Based on (2'-Aminoethyl)carbostyril and (2'-Aminoethyl)-1-hydroxy-2-pyridone Systems

  • Yoon, Sung-Hwa
    • Journal of Pharmaceutical Investigation
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    • v.22 no.3
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    • pp.49-63
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    • 1992
  • Two different types of chemical manipulations of dobutamine were investigated in order to develop novel, improved cardiotonic drugs. Three new analogues of carbostyril, in which the m-hydroxy group of dobutamine was isosterically modified with an amide type carbostyril system, were synthesized from, ${\rho}-methoxyphenethylamine$ via multi-steps. Two analogues of (2'-aminoethyl)-1-hydroxy-2-pyridone system which has isosteric structural similarity with dopamine without having the COMT vulnerable m-hydroxy group were synthesized via 12 synthetic steps. Their biological stabilities in various media and inotropic activities were evaluated.

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Bleaching of Kraft Pulp with Xylanase and Laccase-Mediator System

  • Yoon, Chulhyun;Jung, Hyunchae
    • Journal of Korea Technical Association of The Pulp and Paper Industry
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    • v.46 no.1
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    • pp.1-10
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    • 2014
  • Xylanase (X) derived from Aurreobasidium pullulans and laccase-mediator system (LM) using Trichophyton sp. LKY-7 laccase (TrL) and N-hydroxy-2-pyridone analogue (NHP) as a mediator were applied in hardwood kraft pulp (HwKP) bleaching. The individual and the synergistic effects of X and LM stage were investigated in the enzymatic bleaching of HwKP. Also, the effects of subsequent alkaline extraction (E) and alkaline/hydrogen peroxide treatment (P) were examined. In X or LM treatment alone, an appreciable bleaching effect of HwKP was not observed, whereas subsequent E or P stage enhanced the increase of brightness and the decrease of kappa number. Especially, P stage significantly enhanced the bleaching effect of pulp. Bleaching of HwKP with XLM sequentially gave significantly higher pulp brightness and lower kappa number than that obtained after the treatment of HwKP with X+LM simultaneously. When HwKP was sequentially treated with XLM followed by P stage, the brightness increased by about 11% ISO and the kappa number decreased by about 3.6 in comparison with the initial pulp. Xylanase and laccase were strongly inactivated by NHP both in the absence and the presence of pulp.

Molecular characterization and expression of cytosolic OASTL control cysteine metabolism in Mimosa pudica L.

  • Harun-Ur-Rashid, Md.;Masakazu, Fukuta;Hossain, Md. Amzad;Oku, Hirosuke;Iwasaki, Hironori;Oogai, Shigeki;Anai, Toyoaki
    • Proceedings of the Korean Society of Crop Science Conference
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    • 2017.06a
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    • pp.224-224
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    • 2017
  • In plants, cysteine(Cys) is decisive for protein and glutathione that acts as an indispensable sulfur grantor for methionine and many other sulfur containing secondary products. Cys formation is involved in the consecutive two reactions using two enzymes-serine acetyl transferase (SAT) and O-acetylserine (thiol)lyase (OASTL) and appeared in plant cytosol, chloroplast and mitochondria. OASTL is able to produce mimosine with 3-hydroxy-4-pyridone (3H4P) in lieu of $H_2S$ for Cys. In this report, we describe the first time cloning, purification and characterization of cytosolic(cy)OASTL from M. pudica and its expression in Escherichia coli and try to find out the cross link between this OASTL and the mimosine formation and to elucidate the metabolic role of cy-OASTL in M. pudica. The purified recombinant protein was 34.7 KDa. The optimum reaction pH and temperature was 6.5 and $50^{\circ}C$, respectively. The Michaelis constant (Km) and the Vmax value of the enzyme was $252{\pm}25{\mu}M$ and $57{\pm}3{\mu}M\;cysteine\;min^{-1}\;{\mu}g\;protein^{-1}$ for sulfide and $159{\pm}21{\mu}M$ and $58{\pm}2.4{\mu}M\;cysteine\;min^{-1}\;{\mu}g\;protein^{-1}$ for OAS subsequently. After cleaving the His-tag, we tried to observe cy-OASTL to form mimosine with appropriate substrate but it was not successful. It may be concluded that cy-OASTL of the present study is only Cys specific, not mimosine.

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Molecular characterization and docking dynamics simulation prediction of cytosolic OASTL switch cysteine and mimosine expression in Leucaena leucocephala

  • Harun-Ur-Rashid, Md.;Masakazu, Fukuta;Amzad Hossain, Md.;Oku, Hirosuke;Iwasaki, Hironori;Oogai, Shigeki;Anai, Toyoaki
    • Proceedings of the Korean Society of Crop Science Conference
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    • 2017.06a
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    • pp.36-36
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    • 2017
  • Out of twenty common protein amino acids, there are many kinds of non protein amino acids (NPAAs) that exist as secondary metabolites and exert ecological functions in plants. Mimosine (Mim), one of those NPAAs derived from L. leucocephala acts as an iron chelator and reversely block mammalian cell cycle at G1/S phases. Cysteine (Cys) is decisive for protein and glutathione that acts as an indispensable sulfur grantor for methionine and many other sulfur-containing secondary products. Cys biosynthesis includes consecutive two steps using two enzymes-serine acetyl transferase (SAT) and O-acetylserine (thiol)lyase (OASTL) and appeared in plant cytosol, chloroplast, and mitochondria. In the first step, the acetylation of the ${\beta}$-hydroxyl of L-serine by acetyl-CoA in the existence of SAT and finally, OASTL triggers ${\alpha}$, ${\beta}$-elimination of acetate from OAS and bind $H_2S$ to catalyze the synthesis of Cys. Mimosine synthase, one of the isozymes of the OASTLs, is able to synthesize Mim with 3-hydroxy-4-pyridone (3H4P) instead of $H_2S$ for Cys in the last step. Thus, the aim of this study was to clone and characterize the cytosolic (Cy) OASTL gene from L. leucocephala, express the recombinant OASTL in Escherichia coli, purify it, do enzyme kinetic analysis, perform docking dynamics simulation analysis between the receptor and the ligands and compare its performance between Cys and Mim synthesis. Cy-OASTL was obtained through both directional degenerate primers corresponding to conserved amino acid region among plant Cys synthase family and the purified protein was 34.3KDa. After cleaving the GST-tag, Cy-OASTL was observed to form mimosine with 3H4P and OAS. The optimum Cys and Mim reaction pH and temperature were 7.5 and $40^{\circ}C$, and 8.0 and $35^{\circ}C$ respectively. Michaelis constant (Km) values of OAS from Cys were higher than the OAS from Mim. Inter fragment interaction energy (IFIE) of substrate OAS-Cy-OASTL complex model showed that Lys, Thr81, Thr77 and Gln150 demonstrated higher attraction force for Cys but 3H4P-mimosine synthase-OAS intermediate complex showed that Gly230, Tyr227, Ala231, Gly228 and Gly232 might provide higher attraction energy for the Mim. It may be concluded that Cy-OASTL demonstrates a dual role in biosynthesis both Cys and Mim and extending the knowledge on the biochemical regulatory mechanism of mimosine and cysteine.

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