Analogs of carbohydrate metabolism coenzymes

Summary 1. The synthesis of the isocytidine diphosphate -D-glucopyranose analog of uridine diphosphate glucose modified at C₂ of the heterocyclic ring has been described.2. The preparation of nucleotides that are derivatives of isocytidine has been reported for the first time.Khimiya Prirodnykh Soedinenii, Vol. 1, No. 5, pp. 328–334, 1965     

Analogs of coenzymes of carbohydrate metabolism

Conclusions Three analogs of adenosine diphosphate glucose with a modified nucleoside residue were synthesized: inosin diphosphate glucose,xanthosine diphosphate glucose, and 2-deoxyadenosine triphosphate glucose.For communication 13, see [1].Translated from Izvestiya Akademii Nauk SSSR, Seriya Khimicheskaya, No. 12, pp. 2775–2779, December, 1969.     

Analogs of coenzymes of carbohydrate metabolism

Summary The transphosphorylation reaction taking place in the interaction of diseryl pyrophosphates with acetic acid and glycine has been studied. It has been found that the rate of this reaction depends on the pH of the medium and on the presence of metal ions. A high reactivity of the pyrophosphate bond in the transphorylation reaction has been found which exceeds the reactivity of a natural compound with a high-energy bond, ATP.Khimiya Prirodnykh Soedinenii, Vol. 3, No. 2, pp. 126–131, 1967     

Analogs of coenzymes of carbohydrate metabolism

Summary The synthesis of 2-thiouridine diphosphate -D-glucopyranose, a new analog of uridine diphosphate glucose, has been described.Khimiya Prirodnykh Soedinenii, Vol. 1, No. 6, pp. 409–414, 1965     

Analogs of carbohydrate-metabolish coenzymes. Communication 4. Synthesis of 6-azauridine diphosphate glucose

Summary The synthesis is described of a new UDPG analog, 6-azauridine diphosphate glucose.The authors are deeply grateful to the group of workers at the Institute of Organic Chemistry and Biochemistry of the Czechoslovakian Academy of Sciences, headed by Dr. Smrt, for placing a preparation of 6-azauridine at our disposal.Translated from Izvestiya Akademii Nauk SSSR, Seriya Khimicheskaya, No. 7, pp. 1236–1241, July, 1964     

Analogs of coenzymes of carbohydrate metabolism

Summary 1. The synthesis of N₁-methyl-ADGP, an analog of the natural coenzyme adenosine diphosphate glucose, has been synthesized.2. On the basis of an analysis of the UV spectra and the electrophoretic mobility of derivatives of N₁-methyladenosine, the hypothesis has been put forward that at pH 7.5 it exists in solutions in the protonated form.Khimiya Prirodnykh Soedinenii, Vol. 4, No. 2, pp. 123–128, 1968For communication VIII, see [1].     

Palladium-assisted carbohydrate reactions I. Sodium cyanoborohydride-promoted allylic rearrangements of C-6 substituted pyranoside glycals.

Methoxypalladation of C-6 substituted pyranoside glycals followed by addition of sodium cyanoborohydride gives allylic rearrangement products in good yield with excellent regio-and stereoselectivity.     

Heterocyclic analogs of 5,12-naphthacenequinone. 5. Synthesis of 2,3-diamino-1,4-dimethoxyanthraquinone and its heterocyclic derivatives

A new method for the synthesis of 2,3-diamino-1,4-dimethoxyanthraquinone from quinizarin has been developed. Heterocyclic analogs of 5,12-naphthacenequinone have been synthesized based on this o-diamine-4,11-dimethoxyanthra[2,3-d]imidazole-5,10-dione, 4,11-dimethoxyanthra[2,3-d][1,2,3]triazole-5,10-dione, and 5,12-dimethoxynaphtho[2,3-g]quinoxaline-6,11-dione. On the 70th Birthday of Professor E. Lukevics. __________ Translated from Khimiya Geterotsiklicheskikh Soedinenii, No.1, 96–102, January 2007.     

Glycopeptides. Communication 12. Some properties of carbohydrate amino-acyl derivatives containing an amide link

Conclusions The stabilities of the amide links of amino-acyl derivatives of amino sugars, glucosylamine, and galacturonic acid were investigated. All these types of amide link differ little from the usual amide link in peptides, and they are stable over a wide pH range.Translated from Izvestiya Akademii Nauk SSSR, Seriya Khimicheskaya, No. 8. pp. 1400–1404, August, 1966.     

Synthesis of macroheterocyclic analogs of dibenzocrown ethers. 5. 16- and 17-Membered oxaazacrown ethers

Macrocyclic diamides are synthesized by condensation of 1,5-bis(2-aminophenyl)-1,5-dioxapentane and 1,6-bis(2-aminophenyl)-1,6-dioxahexane with the dichlorides of glutaric, diglycolic, thiodiglycolic, and N-tosyliminodiacetic acids under high dilution conditions. Reduction with diborane gives the 16- and 17-membered dibenzodiazacrown ethers. The structure of the compounds synthesized is confirmed by IR,NMR (¹H and ¹³C), and mass spectral data.For Communication 4, see [1].Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 5, pp. 691–696, May, 1990.     

Analogs of pyrimidine nucleosides. 17. Synthesis of 1-[5(2)-fluoromethyltetrahydro-2-furyl]uracils

The synthesis of 2-fluoromethyltetrahydrofuran is described, and it is shown that chlorination of the latter gives 2-chloro-5- and 2-chloro-2-fluoromethyltetrahydrofurans in a ratio of 5:1. 2,4-Bis(trimethylsilyl) derivatives of uracil were alkylated by means of the mixture of -chloro ethers without separation, and a mixture of the cis and trans isomers of 1-(5-fluoromethyltetrahydro-2-furyl)uracils and 1-(2-fluoromethyltetrahydro-2-furyl)uracils were obtained. The reaction products were identified on the basis of the PMR spectra.See [1] for communication 16.Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 2, pp. 256–259, February, 1982.