- Large-scale synthesis of (E)-4-amino-2-methylbut-2-en-1-ol: Key building block for the synthesis of trans-zeatin
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In this paper a large-scale synthesis of (E)-4-amino-2-methylbut-2-en-1-ol was disclosed and trans-zeatin could be accessed on industrial scale.
- Pei, Jianyun,Li, Jie,Xie, Yan,Weng, Jiangsen,Ge, Chengsheng,Wang, Shuhua
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- A purine nucleoside phosphorylase in Solanum tuberosum L. (potato) with specificity for cytokinins contributes to the duration of tuber endodormancy
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StCKP1 (Solanum tuberosum cytokinin riboside phosphorylase) catalyses the interconversion of the N9-riboside form of the plant hormone CK (cytokinin), a subset of purines, with its most active free base form. StCKP1 prefers CK to unsubstituted aminopurines. The protein was discovered as a CK-binding activity in extracts of tuberizing potato stolon tips, from which it was isolated by affinity chromatography. The N-terminal amino acid sequence matched the translation product of a set of ESTs, enabling a complete mRNA sequence to be obtained by RACE-PCR. The predicted polypeptide includes a cleavable signal peptide and motifs for purine nucleoside phosphorylase activity. The expressed protein was assayed for purine nucleoside phosphorylase activity against CKs and adenine/adenosine. Isopentenyladenine, trans-zeatin, dihydrozeatin and adenine were converted into ribosides in the presence of ribose 1-phosphate. In the opposite direction, isopentenyladenosine, trans-zeatin riboside, dihydrozeatin riboside and adenosine were converted into their free bases in the presence of Pi. StCKP1 had no detectable ribohydrolase activity. Evidence is presented that StCKP1 is active in tubers as a negative regulator of CKs, prolonging endodormancy by a chill-reversible mechanism.
- Bromley, Jennifer R.,Warnes, Barbara J.,Newell, Christine A.,Thomson, Jamie C.P.,James, Celia M.,Turnbull, Colin G.N.,Hanke, David E.
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- Preparation method of zeatin
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The invention provides a preparation method of zeatin, which relates to the technical field of organic synthesis, the preparation method comprises the following steps: reducing 6-trans-(3-methyl-2-alkene-4-butyrate)group-aminopurine to prepare zeatin; according to the brand-new zeatin synthesis route provided by the invention, 6-trans-(3-methyl-2-alkene-4-butyrate)-aminopurine is used as a raw material, is a relatively good solid, is easy to treat, relatively few in synthesis route steps, relatively high in yield and easy to produce and amplify, and further can realize industrial production.
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- Synthesis method of (E)-4-hydroxy-3-methyl-2-butenylamine and zeatin
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The invention relates to a synthetic method of (E)-4-hydroxyl-3-methyl-2-butenylamine and zeatin. The synthesis method of (E)-4-hydroxy-3-methyl-2-butenylamine comprises the following steps: synthesizing a compound I from (E)-1,4-dibromo-2-methylbutyl-2-ene, wherein the chemical formula of the compound I is as described in the specification; adding acetate and a solvent into the compound I, performing a reaction under an inert gas condition until the reaction is finished; then adding an alkaline solution, conducting a reaction until the reaction is finished; and finally, adding concentrated hydrochloric acid and a solvent, conducting a reaction under an inert gas condition until the reaction is finished, and carrying out purification. Compared with the prior art, the method has the advantages that reaction steps are simple, amino groups do not need to be protected, purification of (E)-4-hydroxy-3-methyl-2-butenylamine can be achieved through distillation after the reaction is finished,and production cost is reduced.
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- Method for synthesizing adenine and derivatives thereof
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The invention discloses a method for synthesizing adenine and derivatives thereof. The method comprises the steps: firstly, subjecting diethyl malonate and dimethyl dioxirane to an oxidation reaction, so as to obtain 2-hydroxyldiethyl malonate; then, carrying out an ammonolysis reaction with ammonia water, so as to obtain 2-hydroxyl malonamide; then, carrying out a cyclization reaction with trimethyl orthoformate, so as to obtain 5-hydroxyl pyrimid-4,6-(1H,5H)-dione; then, carrying out a chlorination reaction with phosgene, so as to obtain 4,5,6-trichloropyrimidine; then, carrying out a cyclization reaction with formamidine hydrochloride, so as to obtain 4-chloro-1H-pyrazol[3, 4-d]pyrimidine; finally, carrying out an ammoniation reaction with ammonia water or an amine compound in the presence of triethylamine, thereby obtaining the adenine and derivatives thereof. According to the method, the raw materials are moderately-priced and readily available, the reaction conditions are mild, the reaction process is safe, the requirements on production equipment are low, particularly, the environmental pollution is light, and the yield is relatively high, so that the method is applicable to industrial large-scale production.
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Paragraph 0047; 0048
(2017/07/19)
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- A hetero diels-alder access to (Z)-zeatin and (Z)-isozeatin
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(Z)-6-(4-Hydroxy-3-methylbut-2-en-1-ylamino)purine, (Z)-zeatin, and the isomeric (Z)-isozeatin, both free from the E isomers, were prepared using the cycloaddition of the in situ generated tert-butyl nitrosoformate on isoprene. A mixture of tert-butyl 5(and 4)-methyl-3,6-dihydro-2H-1,2-oxazine-2-carboxylates thus formed was deprotected and reductively cleaved to (Z)-4-amino-2(and 3)-methylbut-2-en-1-ols, which were chromatographically separated and finally alkylated with 6-chloropurine to give the title compounds.
- Tolman, Vladimir,Hanus, Jan,Sedmera, Petr
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p. 696 - 702
(2007/10/03)
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- Syntheses of cis-zeatin and its 9-(2-deoxy-β-D-ribofuranosyl) derivative: A novel synthetic route to the side chain at C(6), and cytokinin activity
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cis-Zeatin (3a) and its 9-(2-deoxy-β-D-ribofuranosyl) derivative (3c) have been synthesized from N-[(1,1-dimethylethoxy)carbonyl]glycine methyl ester (5) in 5 steps by adopting the 'α-amino aldehyde/olefination' technology. The new cis-zeatin derivative (3c), its trans isomer (1c), and known trans-zeatin 9-β-D-riboside (1b) were tested for cytokinin activity in the stimulation of chlorophyll biosynthesis in etiolated cucumber cotyledons. The ribeside 1b turned out to be the most active cytokinin among them, while the deoxyribosides 1c and 3c showed a marked decrease and a total loss, respectively, of cytokinin activity.
- Evidente,Piccialli,Sisto,Ohba,Honda,Fujii
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p. 1937 - 1939
(2007/10/02)
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- THE SYNTHESIS OF L(-) AND D(+) LUPINIC ACID
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Optically active L-lupinic acid (e.e. > 95percent) and D-Lupinic acid amide were obtained by enantioselective hydrolysis of a racemic mixture of the amide of D,L-lupinic acid with aminopeptidase from Pseudomonas putida.Hydrolysis of D-Lupinic acid amide gave D-Lupinic acid.
- Shadid, Belal,Plas, H. C. van der,Boesten, W. H. J.,Kamphuis, J.,Meijer, E. M.,Schoemaker, H. E.
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p. 913 - 920
(2007/10/02)
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- Cytokinin metabolism and the modulation of cytokinin activity in radish
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The metabolism of zeatin, N6-(Δ2-isopentenyl) adenine, dihydrozeatin, zeatin-O-glucoside and dihydrozeatin-O-glucoside has been studied using derooted radish seedlings. The metabolites were identified by UV and GC/MS. The patterns of metabolism are compared and provide evidence that the O-glucosyl conjugates may be storage forms of the cytokinins.
- McGaw, Brian A.,Horgan, Roger,Heald, Jim K.
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