The Ring Structure of Thymidine

Levene, P. A.; Tipson, R. Stuart

doi:10.1126/science.81.2091.98

Cited by 30 publications

(32 citation statements)

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“…In the coenzymes position 5 of the carbohydrate is favored by nature, while the hydrolytic fragments of ribonucleic acid are 3'-phosphate esters (see formulas 18). Attachment of the phosphoric acid at carbon atom 3 of the ribose has been proved for the adenine and guanine nucleotides (241), and the same position of the phosphoric acid in the pyrimidine ribose nucleotides is ascertained by synthesis (254). The borderline between coenzymes and the other ribonucleotides is not altogether sharp.…”

Section: A Ribose Nucleotidesmentioning

confidence: 92%

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Chemistry and Enzymology of Nucleic Acids

Schlenk

1949

Advances in Enzymology - And Related Areas of Molecular Biology

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Section: A Ribose Nucleotidesmentioning

confidence: 92%

“…The furanoid structure of the carbohydrate could be established (183,253) and P-ribosidic linkage is probable (83). ( 4 4 ) , uncl in thymidine a furanoid ring structure could be established (255). The identity of the sugar with D-2-desoxyribose remains to be dcnionstrated.…”

Section: Pyrimidine Ribosides and Desoxyribosidesmentioning

confidence: 99%

Chemistry and Enzymology of Nucleic Acids

Schlenk

1949

Advances in Enzymology - And Related Areas of Molecular Biology

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“…Nucleophilic displacement reactions of nucleoside derivatives are well established owing to the accessibility of precursor sulfonate esters and halides [1]. Displacements with a diverse variety of both hard and soft nucleophiles have enabled the construction of natural products [2–3] and their analogues [4–6].…”

Section: Introductionmentioning

confidence: 99%

Nucleophilic displacement reactions of 5′-derivatised nucleosides in a vibration ball mill

Eguaogie¹,

Conlon²,

Ravalico³

et al. 2017

Beilstein J. Org. Chem.

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Vibration ball-milling in a zirconia-lined vessel afforded clean and quantitative nucleophilic displacement reactions between 4-methoxybenzylthiolate salts and nucleoside 5′-halides or 5′-tosylates in five to 60 minutes. Under these conditions, commonly-encountered nucleoside cyclisation byproducts (especially of purine nucleosides) were not observed. Liquid-assisted grinding of the same 5'-iodide and 5′-tosylate substrates with potassium selenocyanate in the presence of DMF produced the corresponding 5′-selenocyanates in variable yields over the course of between one and eleven hours thereby avoiding the preparation and use of hygroscopic tetrabutylammonium salts.

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“…55 The enzymic synthesis of inosine and guanosine from the corresponding purines and ribose 1-phosphate has been accomplished using enzymes (nucleoside phosphorylases) obtained from the liver tissue of rats. 66 The synthesis is of particular interest because it probably represents the process by which nucleosides are synthesized naturally. Structure of Nucleosides.…”

Section: Ch 3 -Ceh 4 -Nh Ch 3 -C 6 H 4 -Nhmentioning

confidence: 99%

“…65 The principal evidence for the type of ring structure of these nucleosides is that trityl derivatives are formed. 66 Hence, the sugar rings are probably of the furanose type.…”

Section: Ch 3 -Ceh 4 -Nh Ch 3 -C 6 H 4 -Nhmentioning

confidence: 99%

Nitrogenous Derivatives

1948

Chemistry of the Carbohydrates

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HCNH 2 I I ο HCOH I NITROGENOUS DERIVATIVES 377 An isomeric acetamide derivative has been prepared by the action of ammonia on aldehydo-ghicose pentaacetate; 45 lead tetraacetate oxidation shows that it has a furanose structure. Evidently, the ammonia combines with the aldehyde group and an acetyl group migrates to the amino group from the 4-position. Diacetamide derivatives may result 4 from the action of ammonia on the acetylated nitriles (Wohl degradation), a process in which a carbon atom is lost. These substances probably have open-chain structures. CN HCOAc JÜ!-> HC(NHAc), + NH 4 CN AcOCH AcOCH I IAlthough the ring forms exist, many of the properties of the glycosylamines are better interpreted on the basis of the imine structure, and it seems probable that the two structures are in equilibrium. In contrast to the desoxy sugar amines, in which the amino group replaces the primary or secondary hydroxyls, the osimines are hydrolyzed by dilute acids and are reduced to 1-amino alcohols. 6 B. N-Glycosides. Schiff, in studying the reactions of amines with aldehydes, found that condensation products, the so-called Schiff bases, are formed. R-CHO + R'-NH 2 -R-CH=N-R' (Schiff base)When the reaction first was applied to the sugars, amorphous products were obtained which were considered to have the Schiff base structure. Crystalline materials later were prepared 7 by heating glucose or fructose in an alcoholic solution of aniline. Sorokin believed these substances, frequently called sugar anilides, to have ring structures and to be analogous to the glycosides. It seems probable that the crystalline materials are N-glycosides but that in solution they are in equilibrium with the corresponding Schiff base and possibly with the anomeric (alpha-beta) and ring isomers. RNHCH

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The Ring Structure of Thymidine

Cited by 30 publications

References 0 publications

Chemistry and Enzymology of Nucleic Acids

Chemistry and Enzymology of Nucleic Acids

Nucleophilic displacement reactions of 5′-derivatised nucleosides in a vibration ball mill

Nitrogenous Derivatives

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