Quinoxalines derived from D-glucose and O-phenylenediamine in a weakly acidic medium.

Morita, Naofumi; Inoue, Keiichi; Takagi, Masanosuke

doi:10.1271/bbb1961.45.2665

Cited by 18 publications

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“…Two main peaks (designated GA-I and G-2) were obtained, in addition to those of M-l and the internal standard. GA-I was identified as 2-(2 1 ,3 1 -dihydroxypropyl)-3-methylquinoxaline, by the agreement of the Rf values, the colorization of TLC spots, the fragmentation patterns by GC-MS analysis, and by some other analytical data, as has been reported previously.5) Likewise, G-2 was established to be 2_(2 1 ,3 1 -dihydroxypropyl) quinoxaline. The yields of GA-I and G-2 formed were estimated to be about 16% and An aliquot of a 3 hr reaction mixture of M-1 (5 mM) in an alkaline buffer (0.2 M carbonate, pH 10) at 100°C was extracted with n-butanol, and then evaporated to dryness.…”

Section: Chemicalssupporting

confidence: 65%

“…5 ) Quinoxalines having one hydroxymethyl group instead of a longer side chain may exhibit such structural conversion. Furthermore, in the course .of quinoxaline formation from maltose, amylose, lichenan and barley glucan,6) the main quinoxaline derivative, 2-(2 / ,3 1 -dihydroxypropyl)-3-hydroxymethylquinoxaline (M-l) was found to be relatively unstable, compared with other quinoxaline derivatives possessing four carbon atoms in one of their side chains.…”

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confidence: 99%

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Structural Changes of Quinoxaline Derivatives, with Special Reference to 2-(2^″,3^″-Dihydroxypropyl)-3-hydroxy-methylquinoxaline in Alakaline and Acidic Solutions

Morita

Inoue

Hayashi

1983

Agricultural and Biological Chemistry

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Section: Chemicalssupporting

confidence: 65%

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confidence: 99%

Structural Changes of Quinoxaline Derivatives, with Special Reference to 2-(2^″,3^″-Dihydroxypropyl)-3-hydroxy-methylquinoxaline in Alakaline and Acidic Solutions

Morita

Inoue

Hayashi

1983

Agricultural and Biological Chemistry

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“…14,21,39 The reducing strength of glucose, however, is compromised in the presence of oPDA due to a condensation reaction. 41 The synthesis results 12/20 from different reducing conditions are summarized in Table 1. Pre-reduction of Cu (II) to Cu (I) is the key step to synthesize Cu NWs in a mild condition.…”

Section: /20mentioning

confidence: 99%

Synthesis of oxidation-resistant electrochemical-active copper nanowires using phenylenediamine isomers

et al. 2019

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Phenylenediamine (PDA) was chosen as a coordinating, reducing, and capping agent to effectively direct growth and protect against oxidation of Cu nanowires (Cu NWs) in an aqueous solution. PDA was found to reduce Cu (II) to Cu (I) at room temperature, and stabilize the resulting Cu (I) by forming a coordination complex. The presence of a stable Cu (I) complex is the key step in the synthesis of Cu NWs under mild conditions. Different PDA isomers lead to different growth paths of forming Cu NWs. Both pPDA and mPDA-synthesized Cu NWs were covered with a thin layer of polyphenylenediamine and show excellent anti-oxidation properties, even in the presence of water. The usefulness of the present and electrochemical active Cu NWs for a variety of nanotechnology applications is discussed.

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“…The final reaction volume was 100 l and the reaction temperature was 35°C unless otherwise stated. The concentration of the reaction substrate, DK-MTP-1-P, was calculated on the basis of the reaction characteristics between 2,3-butanedione and o-phenylenediamine (37,38). The concentration of the reaction product, 2-hydroxy-3-keto-5-methylthiopentenyl 1-phosphate was monitored spectrophotometrically at 280 nm (20,24,33,34).…”

Section: Expression and Purification Of Recombinant Rlps And Mutated mentioning

confidence: 99%

Structural and Functional Similarities between a Ribulose-1,5-bisphosphate Carboxylase/Oxygenase (RuBisCO)-like Protein from Bacillus subtilis and Photosynthetic RuBisCO

Saito

Ashida

Sakiyama

et al. 2009

Journal of Biological Chemistry

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The sequences classified as genes for various ribulose-1,5-bisphosphate (RuBP) carboxylase/oxygenase (RuBisCO)-like proteins (RLPs) are widely distributed among bacteria, archaea, and eukaryota. In the phylogenic tree constructed with these sequences, RuBisCOs and RLPs are grouped into four separate clades, forms I-IV. In RuBisCO enzymes encoded by form I, II, and III sequences, 19 conserved amino acid residues are essential for CO 2 fixation; however, 1-11 of these 19 residues are substituted with other amino acids in form IV RLPs. Among form IV RLPs, the only enzymatic activity detected to date is a 2,3-diketo-5-methylthiopentyl 1-phosphate (DK-MTP-1-P) enolase reaction catalyzed by Bacillus subtilis, Microcystis aeruginosa, and Geobacillus kaustophilus form IV RLPs. RLPs from Rhodospirillum rubrum, Rhodopseudomonas palustris, Chlorobium tepidum, and Bordetella bronchiseptica were inactive in the enolase reaction. DK-MTP-1-P enolase activity of B. subtilis RLP required Mg 2؉ for catalysis and, like RuBisCO, was stimulated by CO 2 . Four residues that are essential for the enolization reaction of RuBisCO, Lys 175 , Lys 201 , Asp 203 , and Glu 204 , were conserved in RLPs and were essential for DK-MTP-1-P enolase catalysis. Lys 123 , the residue conserved in DK-MTP-1-P enolases, was also essential for B. subtilis RLP enolase activity. Similarities between the active site structures of RuBisCO and B. subtilis RLP were examined by analyzing the effects of structural analogs of RuBP on DK-MTP-1-P enolase activity. A transition state analog for the RuBP carboxylation of RuBisCO was a competitive inhibitor in the DK-MTP-1-P enolase reaction with a K i value of 103 M. RuBP and D-phosphoglyceric acid, the substrate and product, respectively, of RuBisCO, were weaker competitive inhibitors. These results suggest that the amino acid residues utilized in the B. subtilis RLP enolase reaction are the same as those utilized in the RuBisCO RuBP enolization reaction.Ribulose-1,5-bisphosphate carboxylase/oxygenase (RuBisCO) 4 catalyzes the carboxylation and oxygenation reactions of ribulose 1,5-bisphosphate (RuBP) in photosynthesis (1-4). This enzyme is the sole CO 2 -fixing enzyme in plants; however, it has certain inefficiencies. It has a very low turnover rate, a low affinity for the substrate, CO 2 , and low specificity between the carboxylation and oxygenation reactions (5-7). Thus, the intrinsic enzymatic properties of RuBisCO are inadequate for efficient incorporation of CO 2 into organic matter in photosynthesis (7). However, plants have overcome these disadvantages by investing a huge amount of leaf nitrogen in RuBisCO synthesis (8).In nature, there are wide variations in the properties and primary sequences of RuBisCO among different photosynthetic organisms (9 -12). The primary sequences vary as much as 73% without loss of activity. The relative specificity ranges from ϳ0.5 in a small subunitless RuBisCO to 238 in a red algal, hexadecameric RuBisCO (13,14). The affinity for CO 2 varies some 100-fold (15). Comparisons ...

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Quinoxalines derived from D-glucose and O-phenylenediamine in a weakly acidic medium.

Cited by 18 publications

References 0 publications

Structural Changes of Quinoxaline Derivatives, with Special Reference to 2-(2^″,3^″-Dihydroxypropyl)-3-hydroxy-methylquinoxaline in Alakaline and Acidic Solutions

Structural Changes of Quinoxaline Derivatives, with Special Reference to 2-(2^″,3^″-Dihydroxypropyl)-3-hydroxy-methylquinoxaline in Alakaline and Acidic Solutions

Synthesis of oxidation-resistant electrochemical-active copper nanowires using phenylenediamine isomers

Structural and Functional Similarities between a Ribulose-1,5-bisphosphate Carboxylase/Oxygenase (RuBisCO)-like Protein from Bacillus subtilis and Photosynthetic RuBisCO

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Quinoxalines derived from D-glucose and O-phenylenediamine in a weakly acidic medium.

Cited by 18 publications

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Structural Changes of Quinoxaline Derivatives, with Special Reference to 2-(2″,3″-Dihydroxypropyl)-3-hydroxy-methylquinoxaline in Alakaline and Acidic Solutions

Structural Changes of Quinoxaline Derivatives, with Special Reference to 2-(2″,3″-Dihydroxypropyl)-3-hydroxy-methylquinoxaline in Alakaline and Acidic Solutions

Synthesis of oxidation-resistant electrochemical-active copper nanowires using phenylenediamine isomers

Structural and Functional Similarities between a Ribulose-1,5-bisphosphate Carboxylase/Oxygenase (RuBisCO)-like Protein from Bacillus subtilis and Photosynthetic RuBisCO

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Structural Changes of Quinoxaline Derivatives, with Special Reference to 2-(2^″,3^″-Dihydroxypropyl)-3-hydroxy-methylquinoxaline in Alakaline and Acidic Solutions

Structural Changes of Quinoxaline Derivatives, with Special Reference to 2-(2^″,3^″-Dihydroxypropyl)-3-hydroxy-methylquinoxaline in Alakaline and Acidic Solutions