5-methyl-3 (2H)-furanone from acid-catalyzed solvolysis of 2-deoxy-D-ribose

Seydel, Joachim K.; Garrett, Edward R.; Diller, Werner; Schaper, Klaus‐Jürgen

doi:10.1002/jps.2600560714

Cited by 22 publications

(3 citation statements)

References 14 publications

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“…In addition, several furanoid compounds (2-5, not detectable in the RNA system) were formed in remarkable quantities from DNA: The predominant 5-methyl-3(2H)-furanone (4) was purified by preparative GC and identified by GC/MS and NMR; R-and β-angelica lactone (2 and 3) as well as 5 were determined by GC/MS. The furanone 4 has previously been shown to arise from 2-deoxyribose by an acid-catalyzed reaction (1 N HCl, 80 °C) (Seydel et al, 1967). Of course, under mild conditions RNA and DNA show strongly reduced reactivity.…”

Section: Resultsmentioning

confidence: 99%

Maillard Reaction of Free and Nucleic Acid-Bound 2-Deoxy-d-ribose and d-Ribose with ω-Amino Acids

Wondrak

Tressl

Rewicki

1997

J. Agric. Food Chem.

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The Maillard reaction of free and nucleic acid-bound 2-deoxy-D-ribose and D-ribose with ω-amino acids (4-aminobutyric acid, 6-aminocaproic acid) was investigated under both stringent and mild conditions. Without (with) amines 2-deoxy-D-ribose (D-ribose) displays the strongest browning activity, and DNA is much more reactive than RNA. From stringent reaction between 2-deoxy-Dribose (or DNA) and methyl 4-aminobutyrate, methyl 4-[2-[(oxopyrrolidinyl)methyl]-1-pyrrolyl]butyrate (12) was identified by GC/MS and NMR as a new 2-deoxy-D-ribose specific key compound trapped by pyrrolidone formation. Levulinic acid-related N-substituted lactames 13-15 were identified as predominant products from DNA with amino acids, whereas RNA paralleled the reaction with D-ribose. R-Angelica lactone (2), a significant degradation product of DNA, and thiols leads under mild conditions to new addition products (e.g., 17 with glutathione). Probable reaction pathways considering activating effects of the polyphosphate backbone of nucleic acids are discussed.

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Section: Resultsmentioning

confidence: 99%

Maillard Reaction of Free and Nucleic Acid-Bound 2-Deoxy-d-ribose and d-Ribose with ω-Amino Acids

Wondrak

Tressl

Rewicki

1997

J. Agric. Food Chem.

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“…where k is the Boltzmann constant 1.381 X [10][11][12][13][14][15][16] erg deg-1, ñ is the Planck constant, 6.626 X 10-27 erg sec, and R is 1.987 cal deg-1 mol-1. On taking logarithms and rearranging AS* = 2.3037?…”

Section: Resultsmentioning

confidence: 99%

Solvolysis of adenine nucleosides. I. Effects of sugars and adenine substituents on acid solvolyses

Garrett¹,

Mehta²

1972

J. Am. Chem. Soc.

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146

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“…As a precaution, each aliquot was added to excess 0.1 n NaOH solution and allowed to stand for 16 hr at 25°. It had been reported (Garrett et al, 1966;Seydel et a!., 1967) that hydrolysis of deoxyuridine derivatives in HC1 led to the formation of a chromophore which interfered with the spectrophotometric determinations. This chromophore was destroyed by alkaline treatment.…”

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confidence: 99%

Uncatalyzed hydrolysis of deoxyuridine, thymidine, and 5-bromodeoxyuridine

Shapiro¹,

Kang²

1969

Biochemistry

104

100

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The N-glycosyl bonds of deoxyuridine, thymidine, and 5-bromodeoxyuridine undergo slow hydrolysis in aqueous solution, pH 3-7. The reaction rates are independent of the pH in this range, and of the nature and concentration of the buffer. The reactions have positive entropies of activation. A linear correlation exists between the logarithms of the rate constants for the three nucleosides and the ionization constants for the 1-protons of the corresponding bases. It is pro-

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5-methyl-3 (2H)-furanone from acid-catalyzed solvolysis of 2-deoxy-D-ribose

Cited by 22 publications

References 14 publications

Maillard Reaction of Free and Nucleic Acid-Bound 2-Deoxy-d-ribose and d-Ribose with ω-Amino Acids

Maillard Reaction of Free and Nucleic Acid-Bound 2-Deoxy-d-ribose and d-Ribose with ω-Amino Acids

Solvolysis of adenine nucleosides. I. Effects of sugars and adenine substituents on acid solvolyses

Uncatalyzed hydrolysis of deoxyuridine, thymidine, and 5-bromodeoxyuridine

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