藥學科技
(二)報告：Sci-finder
姓名：王羿茹學號：B303098094
檢索主題：Synthesis of Riboflavin 一、查詢結果：
1. Iron assimilation and transcription factor controlled synthesis of riboflavin in plants By: Vorwieger, A.; Gryczka, C.; Czihal, A.; Douchkov, D.; Tiedemann, J.; Mock, H.-P.; Jakoby, M.; Weisshaar, B.; Saalbach, I.; Baeumlein, H.
Source: Planta, Volume: 226, Issue: 1, Pages: 147-158, Journal, 2007, CODEN: PLANAB, ISSN: 0032-0935, DOI: 10.1007/s00425-006-0476-9
Company/Organization: Institute of Plant Genetics and Crop Plant Research (IPK), Gatersleben, Germany, 06466
Accession Number: 2007:530760, CAN 147:230842, CAPLUS Publisher: Springer
Language: English Abstract
Iron homeostasis is vital for many cellular processes and requires a precise regulation. Several iron efficient plants respond to iron starvation with the
excretion of riboflavin and other flavins. Basic helix-loop-helix transcription factors (TF) are involved in the regulation of many developmental processes, including iron assimilation. Here we describe the isolation and characterization of two
Arabidopsis bHLH TF genes, which are strongly induced under iron starvation. Their heterologous ectopic expression causes constitutive, iron starvation
independent excretion of riboflavin. The results show that both bHLH TFs represent an essential component of the regulatory pathway connecting iron deficiency perception and riboflavin excretion and might act as integrators of various stress reactions.
Indexing
Plant Biochemistry (Section 11-2) Section cross-reference(s): 3 Concepts
Protein motifs
bHLH; transcription factors involved in regulatory pathway connecting iron deficiency-induced synthesis and excretion of
riboflavin in plant tissues
excretion; transcription factors involved in regulatory pathway connecting iron deficiency-induced synthesis and excretion
of riboflavin in plant tissues
Basic helix-loop-helix transcription factors
gene bHLH38 and bHLH39; transcription factors involved in regulatory pathway connecting iron deficiency-induced
synthesis and excretion of riboflavin in plant tissues Biological study, unclassified; Biological study
Tumor, plant
hairy root; transcription factors involved in regulatory pathway connecting iron deficiency-induced synthesis and excretion
of riboflavin in plant tissues
Stress, plant
nutrient deficiency, iron; transcription factors involved in regulatory pathway connecting iron deficiency-induced synthesis
and excretion of riboflavin in plant tissues
Protein sequences
of transcription factor bHLH domains; transcription factors involved in regulatory pathway connecting iron deficiencyinduced
synthesis and excretion of riboflavin in plant tissues
Arabidopsis thaliana Leaf
Seedling
transcription factors involved in regulatory pathway connecting iron deficiency-induced synthesis and excretion of
riboflavin in plant tissues Substances
7439-89-6 Iron, biological studies
homeostasis; transcription factors involved in regulatory pathway connecting iron deficiency-induced synthesis and
excretion of riboflavin in plant tissues
Biological study, unclassified; Biological study
83-88-5 Riboflavin, biological studies
transcription factors involved in regulatory pathway connecting iron deficiency-induced synthesis and excretion of
riboflavin in plant tissues
Biological study, unclassified; Biological study Supplementary Terms
iron; deficiency; assimilation; bHLH; transcription; factor; riboflavin; excretion; plant;
Citations
1)Bailey, P; Plant Cell 2003, 15, 2497
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19)Li, L; Plant Mol Biol 2004, 54, 125
20)Ling, H; Proc Natl Acad Sci USA 2002, 99, 13938
21)Littlewood, T; Basic helix-loop-helix transcription factors 1998
22)Lopez-Millan, A; Plant Physiol 2000, 124, 885 23)Marschner, H; J Plant Nutr 1986, 9, 695 24)Massari, M; Mol Cell Biol 2000, 20, 429 25)Mazoch, J; Eur J Biochem 2004, 271, 553 26)Nagarajah, S; Soil Sci 1966, 102, 399
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52)Zhang, J; J Integr Plant Biol 2006, 48, 75
2. Synthesis of riboflavin 5' phosphate sodium (vitamin B2 derivative) By: Bhattacharya, T. K.; Mondal, P.
Source: Journal of the Institution of Engineers (India), Chemical Engineering Division, Volume: 84, Issue: March, Pages: 47-49, Journal, 2004,
CODEN: JECEAF, ISSN: 0020-3351
Company/Organization: Department of Chemical Technology, Calcutta University, Kolkata, India, 700 009
Accession Number: 2004:1072723, CAN 143:153621, CAPLUS Publisher: Institution of Engineers (India)
Language: English Abstract
Riboflavin has been converted to phosphated ester, riboflavin 5'-phosphate sodium, by the phosphorylation of riboflavin
with pyro-phosphoric acid in three steps reaction. The yield is 80.5% of the theor. value and assay shows 84.5% purity in
the product. The water soly. has been increased to 112 mg/mL at 27°C. Indexing
Carbohydrates (Section 33-7) Concepts
synthesis of riboflavin 5'-phosphate sodium via phosphorylation Substances
83-88-5 Riboflavin, reactions
7664-38-2 Orthophosphoric acid, reactions
synthesis of riboflavin 5'-phosphate sodium via phosphorylation Reactant; Reactant or reagent
2466-09-3P Pyrophosphoric acid
synthesis of riboflavin 5'-phosphate sodium via phosphorylation Reactant; Synthetic preparation; Preparation; Reactant or reagent
130-40-5P Riboflavin 5'-phosphate sodium
synthesis of riboflavin 5'-phosphate sodium via phosphorylation Synthetic preparation; Preparation
Supplementary Terms
riboflavin; phosphate; sodium; prepn; phosphorylation; Citations
1)Sebrell, W; The Vitamins 1954, 3, 337
2)Venderveen, E; Remington's Science and Practice of Pharmacy, Vitamins and Other Nutrients 2001, 1810
3)Anon; Encyclopedia of Chemical Technology 1984, 24, 119
4)Marshall; Pharmaceutical Manufacturing Encyclopedia 1988, 2, 996 5)Anon; Analytical Profile of Drug Substances 1990, 19, 457
6)Anon; Indian Pharmacopoeia 1996, 2, 664
3. Biosynthesis of riboflavin. Single turnover kinetic analysis of GTP cyclohydrolase II By: Schramek, Nicholas; Bracher, Andreas; Bacher, Adelbert
Source: Journal of Biological Chemistry, Volume: 276, Issue: 47, Pages: 44157-44162, Journal, 2001, CODEN: JBCHA3, ISSN: 0021-9258, DOI: 10.1074/jbc.M107306200
Company/Organization: Technische Universitat Munchen, Garching, Germany, D-85747
Accession Number: 2001:869476, CAN 136:130675, CAPLUS
Publisher: American Society for Biochemistry and Molecular Biology Language: English
Abstract
GTP cyclohydrolase II catalyzes the conversion of GTP into a mixt. of 2,5-diamino-6-ribosylamino-4(3H)-pyrimidinone 5'-
phosphate (Compd. 2), formate, and pyrophosphate. Moreover, GMP was recently shown to be formed as a minor
product. The major product (Compd. 2) serves as the first committed intermediate in the biosynthesis of the vitamin
riboflavin. Numerous pathogenic microorganisms are absolutely dependent on endogenous synthesis of riboflavin. The
enzymes of this pathway are therefore potential drug targets, and mechanistic studies appear relevant for development
of bactericidal inhibitors. Pre-steady state quenched flow anal. of GTP cyclohydrolase II shows the rate-detg. step to be
located at the beginning of the reaction sequence catalyzed by the enzyme. Thus, GTP is consumed at a rate const. of
0.064 s-1, and the reaction product, Compd. 2, is formed at an apparent rate const. of 0.062 s-1. Stopped flow expts.
monitored by multiwavelength photometry are well in line with these data. 2-Amino-5-formylamino-6-ribosylamino-4(3H)-
pyrimidinone triphosphate can serve as substrate for GTP cyclohydrolase II but does not fulfill the criteria for a kinetically
competent intermediate. A hypothetical reaction mechanism involves the slow formation of a phosphoguanosyl deriv. of the enzyme under release of
pyrophosphate. The covalently bound phosphoguanosyl moiety is proposed to undergo rapid hydrolytic release of formate from the imidazole ring and/or hydrolytic cleavage of the phosphodiester bond.
Indexing
Enzymes (Section 7-4) Concepts
Enzyme kinetics
single turnover kinetic anal. of GTP cyclohydrolase II Substances
56214-35-8 GTP cyclohydrolase II
single turnover kinetic anal. of GTP cyclohydrolase II
Biological study, unclassified; Physical, engineering or chemical process; Physical process; Biological study; Process
86-01-1 5'-GTP
27089-32-3 73477-63-1
substrate; single turnover kinetic anal. of GTP cyclohydrolase II Biological study, unclassified; Biological study
Supplementary Terms
Citations
1)Foor, F; J Biol Chem 1975, 250, 3545
2)Blau, N; Biochem Clin Asp Pteridines 1982, 1, 103 3)Ritz, H; J Biol Chem 2001, 276, 22273
4)Kwon, N; J Biol Chem 1989, 264, 20496 5)Tayeh, M; J Biol Chem 1989, 264, 19654 6)Nichol, C; Annu Rev Biochem 1985, 54, 729
7)Brown, G; Escherichia coli and Salmonella typhimurium 1987, 1, 521 8)Bracher, A; J Biol Chem 1999, 274, 16727
9)Schramek, N; J Biol Chem 2001, 276, 2622 10)Bacher, A; Methods Enzymol 1997, 280, 382
11)Dawson, R; Data for Biochemical Research 3rd Ed 1986, 109
12)Dietrich, R; J Am Chem Soc 1979, 101, 6144 13)Bracher, A; Biochemistry 2001, 40, 7896
4. Synthesis of riboflavin tetrapropanoate by solid superacid sulphate ion on zirconium dioxide
By: Zhao, Jinglian; Zhang, Zhoumei
Source: Xi'an Jiaotong Daxue Xuebao, Volume: 34, Issue: 6, Pages: 80-84, Journal, 2000, CODEN: HCTPDW, ISSN: 0253-987X
Company/Organization: Xi'an Jiaotong University, Xi'an, Peop. Rep. China, 710049 Accession Number: 2000:575300, CAN 133:237734, CAPLUS
Publisher: XiÏan Jiaotong Daxue Xuebao Bianjibu Language: Chinese
Abstract
The riboflavin tetrapropanoate was prepd. with 78.3% yield starting from riboflavin and propionic anhydride. The solid superacid sulfate ion on zirconium dioxide is used as a catalyst. It was found that the catalyst activity was the highest when zirconium oxychloride·8 H2O immersed in 1 mol/L sulfuric acid for 24 h and baked 3 h at 600 degree. The factors
influencing the yield of the esterification of riboflavin and propionic anhydride are discussed. Optimum conditions for reaction involve that riboflavin and propionic anhydride is 1:40 (molar ratio), mass of catalyst is 4.7% of the total system mass, reaction temp. is 85 degree, and reaction time is 3 h.
Indexing
Biomolecules and Their Synthetic Analogs (Section 26-8) Substances
1314-23-4 Zirconium oxide (ZrO2), uses
7664-93-9D Sulfuric acid, uses, TiO2, ZrO2, or Fe2O3 supported
13463-67-7 Titanium oxide, uses
synthesis of riboflavin tetrapropanoate by solid superacid sulfate ion on zirconium dioxide
Catalyst use; Uses
83-88-5 Riboflavin, reactions
123-62-6 Propionic anhydride
synthesis of riboflavin tetrapropanoate by solid superacid sulfate ion on zirconium dioxide
Reactant; Reactant or reagent
7652-80-4P
synthesis of riboflavin tetrapropanoate by solid superacid sulfate ion on zirconium dioxide
Synthetic preparation; Preparation Supplementary Terms
riboflavin; propanoate; prepn; catalysis; solid; superacid; sulfate; ion; zirconium; dioxide; support; catalyst;
5. Enzymic synthesis of riboflavin and FMN specifically labeled with carbon-14 in the xylene ring
By: Sedlmaier, Helmut; Mueller, Franz; Keller, Paul J.; Bacher, Adelbert
Source: Zeitschrift fuer Naturforschung, C: Journal of Biosciences, Volume: 42, Issue: 4, Pages: 425-9, Journal, 1987, CODEN: ZNCBDA, ISSN:
0341-0382
Company/Organization: Tech. Univ. Muenchen, Garching, Fed. Rep. Ger., D-8046 Accession Number: 1987:530408, CAN 107:130408, CAPLUS
Language: English Abstract
The condensation of 3-hydroximino-2-butanone (I) with 5-amino-6-ribitylamino-2,4(1H,3H)-pyrimidinedione (II) yields
6,7-dimethyl-8-ribityllumazine (III). At slightly alk. pH, the CO group of I reacts preferentially with the 5-amino group of II
(regioselectivity, 4:1). Under acidic conditions, the reaction occurs with higher yield and marginal regioselectivity of opposite direction (1:1.4). Appropriately
13C-labeled samples of I give III labeled at C-6a, C-6, C-7 or C-7a. [6a,7a-13C2]III was prepd. by condensation of II with [1,4-13C2]diacetyl. The lumazines III were converted to riboflavin by the enzyme, riboflavin synthase, with almost quant. yield.
By this procedure, any C-atom of the carbocyclic moiety of riboflavin can be selectively labeled with 13C at high abundance. Phosphorylation yields the resp. 13C-labeled riboflavin 5'-phosphate (FMN) samples.
Indexing
Biochemical Methods (Section 9-14) Section cross-reference(s): 33 Substances
107-12-0 Propionitrile
Grignard reaction of, with carbon-13-labeled Me magnesium iodide Reactant; Reactant or reagent
4227-95-6
Grignard reaction with propionitrile or methylation by Analytical study
57-71-6
condensation of, with aminoribitylaminopyrimidinedione Analytical study
23424-28-4
conversion to carbon-13-labeled acetyl chloride Analytical study
9075-82-5 Riboflavin synthase
in carbon-13-labeled riboflavin synthesis Analytical study
110326-21-1P 110326-22-2P 110345-12-5P 110345-13-6P
prepn. and condensation with aminoribitylaminopyrimidinedione Preparation
17014-74-3P
prepn. and condensation with hydroximinobutanone Preparation
110326-29-9P
prepn. and hydrolysis of
Reactant; Preparation; Reactant or reagent
110326-23-3P 110326-24-4P 110326-25-5P 110345-17-0P
110345-18-1P
prepn. and phosphorylation of Synthetic preparation; Preparation
110326-26-6P 110326-27-7P 110326-28-8P
prepn. and reaction with Et nitrite
Reactant; Synthetic preparation; Preparation; Reactant or reagent
1520-57-6P
prepn. and reaction with Et zinc iodide or esterification
Reactant; Synthetic preparation; Preparation; Reactant or reagent
110345-14-7P 110345-15-8P 110345-16-9P 110370-42-8P
prepn. and reaction with riboflavin synthase
Reactant; Synthetic preparation; Preparation; Reactant or reagent
58735-82-3P
prepn. and reaction with trimethylchlorosilane in presence of sodium Reactant; Synthetic preparation; Preparation; Reactant or reagent
110326-30-2P 110326-31-3P 110345-19-2P 110345-20-5P 110345-21-6P prepn. of Preparation 109-95-5 Ethyl nitrite
reaction of, with carbon-13-labeled butanone Reactant; Reactant or reagent
52918-39-5 75599-13-2
redn. of
Reactant; Reactant or reagent Supplementary Terms
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