The preparation and properties of some nitrosamino acids

Lijinsky, William; Keefer, Larry K.; Loo, James

doi:10.1016/s0040-4020(01)93166-7

Cited by 173 publications

(62 citation statements)

References 11 publications

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“…Reportedly, NO-Pro has conformational isomers of E(anti) and Z(syn) distinguishable by means of CD spectrometry because of the partial double bond character of its formally single N-N linkage ( Fig. 3) (11,12). From the identical CD spectra of the present and the reported studies, we identiˆed 1 as E(anti) isomer and 2 as Z(syn) isomer of NO-Pro.…”

Section: Resultssupporting

confidence: 72%

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Nitrosation of Glutathione and Nitration of Tyrosine by N-Nitrosoproline with Ultraviolet Light

Naka

Suzuki

Arimoto‐Kobayashi

2010

Genes and Environment

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N-Nitrosoproline was thought to be nonmutagenic and noncarcinogenic because of its stability. However, it has been reported that N-nitrosoproline releases nitric oxide and shows direct mutagenicity by UV light irradiation. In this study, nitrosation and nitration of glutathione and tyrosine by N-nitrosoproline with UV light are tested. When a neutral solution of N-nitrosoproline and glutathione was irradiated with UV light of 365 nm generated from an 8 W mercury lamp, S-nitrosoglutathione was formed. When a neutral solution of N-nitrosoproline and tyrosine was irradiated with the UV light, a small amount of 3-nitrotyrosine was generated. A similar intensity of UV light of 254 nm induced formation of S-nitrosoglutathione and 3-nitrotyrosine with lesser e‹ciencies. When UV light of 365 nm was irradiated to a neutral mixture of Nnitrosoproline, gluthathione and tyrosine, a similar amount of S-nitrosoglutathione was generated, while the yield of 3-nitrotyrosine greatly decreased. Similar results to the 365 nm UV light irradiation were observed by sunlight. These results suggest that N-nitrosoproline may induce nitrosation and nitration of cellular components in humans with sunlight.

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Section: Resultssupporting

confidence: 72%

“…Materials: N-Nitrosoproline (NO-Pro) was a gift from Dr. M. Mochizuki of Tokyo University of Science who synthesized this compound as described previously (11), and checked the purity as À99z by high performance liquid chromatography (HPLC). Glutathione (GSH) and tyrosine (Tyr) were obtained from Sigma (MO, USA).…”

Section: Methodsmentioning

confidence: 99%

Nitrosation of Glutathione and Nitration of Tyrosine by N-Nitrosoproline with Ultraviolet Light

Naka

Suzuki

Arimoto‐Kobayashi

2010

Genes and Environment

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“…The transfer of the nitroso function to thiols must, of course, decrease the lifetime of N-nitrosotryptophan derivatives, and the question arose about physiological N-nitrosotryptophan concentrations in plasma. Because N-nitroso compounds were found in aortic rat tissues (26) and proline can be nitrosated only at acidic pH values (27,28), one may conclude that N-nitrosotryptophan derivatives represent the major amount of the experimentally identified N-nitroso compounds in vivo. The major amount of N-nitrosotryptophan derivatives would be located in proteins, because the concentrations of low molecular weight, N-terminal blocked tryptophan derivatives like melatonin are very low in plasma (ϳ0.2 nM) (29).…”

Section: Discussionmentioning

confidence: 99%

Formation of S-Nitrosothiols from Regiospecific Reaction of Thiols with N-Nitrosotryptophan Derivatives

Sonnenschein¹,

Groot

Kirsch

2004

Journal of Biological Chemistry

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“…In contrast to the facile photolysis of N-nitroso a-amino acids as described above, N-nitrosonipecotinic acid (13), in ether, alcohol, or aqueous solution did not undergo photodecomposition noticeably even under prolonged irradiation. Nor did N-nitrosopiperidine undergo any significant photodecomposition in methanol when one or several equivalents of acetic acid were added.…”

mentioning

confidence: 74%

“…In the E-configuration 19b, a hydrogen bonding with the lone pair electrons of the nitroso nitrogen is possible but, probably, less strong in view of the sp2 orbital involved. Indeed, in the solid state, all these nitroso a-amino acids are known to have the Z-conformation 19a which is maintained in solution in the cases of 3 and 16 as demonstrated by 'Hand 13C nmr spectroscopy (13,16). However, 1,2,4,9, and 11 isomerize slowly in solution to Z-E mixtures (13,16).…”

mentioning

confidence: 99%

Photochemistry of N-nitroso-N-alkyl amino acids: a facile oxidative decarboxylation

Chow¹,

Horning²,

Polo³

1980

Can. J. Chem.

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Thispaper is dedicated to Prof. Raymond U . Lemieux on the occasion of his 60th birthday YUAN L. CHOW, DOUGLAS P. HORNING, and JOEL POLO. Can. J. Chem. 58,2477Chem. 58, (1980. Several N-alkyl or N-phenyl-N-nitroso a-amino acids were synthesized and were shown to photolytically rearrange to amidoximes with concurrent decarboxylation in solution or solid states without the presence of externally added acids. In contrast, N-nitrosonipecotinic acid, a N-nitroso p-amino acid, as well as N-nitrosopiperidine in the presence of acetic acid were not photolabile. The photolability of N-nitroso a-amino acids was ascribed to the presence of an intramolecular association between the nitrosamino and carboxyl groups through hydrogen bonding. The species having the hydrogen bonding through the nitroso oxygen in the 2-configuration was believed to be photolabile and decomposed to alkylideneimines as the primary product. The mechanism of the oxidative photorearrangement was discussed.

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The preparation and properties of some nitrosamino acids

Cited by 173 publications

References 11 publications

Nitrosation of Glutathione and Nitration of Tyrosine by N-Nitrosoproline with Ultraviolet Light

Nitrosation of Glutathione and Nitration of Tyrosine by N-Nitrosoproline with Ultraviolet Light

Formation of S-Nitrosothiols from Regiospecific Reaction of Thiols with N-Nitrosotryptophan Derivatives

Photochemistry of N-nitroso-N-alkyl amino acids: a facile oxidative decarboxylation

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