関: 6-azauridine

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出典(authority):フリー百科事典『ウィキペディア（Wikipedia）』「2014/11/08 07:06:20」(JST)

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Uridine, a nucleoside, contains an uracil attached to a ribose ring (known as a ribofuranose) via a β-N₁-glycosidic bond.

If uracil is attached to a deoxyribose ring, it is known as a deoxyuridine.

Dietary sources of uridine

Uridine is one of the four basic components of ribonucleic acid (RNA); the other three are adenosine, guanosine, and cytidine. Some foods that contain uridine in the form of RNA are listed below. However virtually none of the uridine in this form is bioavailable, since - as shown by Handschumacher's Laboratory at Yale Medical School in 1981 (Gasser, et al., Science, 1981, 213:777) - it is destroyed in the liver and gastrointestinal tract, and no food, when consumed, has ever been reliably shown to elevate blood uridine levels. In infants consuming mothers'milk or commercial infant formulas, uridine is present as its monophosphate, UMP,^{[citation needed]} and this source of uridine is indeed bioavailable^[1] and enters the blood.^{[citation needed]}

Sugarcane extract^[2]
Tomatoes (0.5 to 1.0 g uridine per kilogram dry weight)^[3]
Brewer’s yeast (1.7% uridine by dry weight)^[4]^[5]
Beer^[6]
Broccoli^[4]
Offal (liver, pancreas, etc.)^[4]

Consumption of RNA-rich foods may lead to high levels of purines (adenosine and guanosine) in blood. High levels of purines are known to increase uric acid production and may aggravate or lead to conditions such as gout. Moderate consumption of yeast, about 5 grams per day, should provide adequate uridine for improved health with minimal side effects.^{[citation needed]}

Note: It has been suggested that the RNA content of yeast products should be chemically reduced if these products are to be consumed in high amounts (50 grams or more per day) as a source of protein. However, such processing is expensive and, as of 2008, commonly available brewer's yeast products were not RNA-reduced.^{[citation needed]}

Harvard researchers report that supplementation in rats with a combination of uridine and EPA/DHA omega-3 fatty acids has antidepressant activity.^[7]

In the glycolysis pathway

Uridine plays a role in the glycolysis pathway of galactose.^[8] There is no catabolic process to metabolize galactose. Therefore, galactose is converted to glucose and metabolized in the common glucose pathway. Once the incoming galactose has been converted into galactose 1-phosphate (Gal-1-P), it is involved in a reaction with UDP-glucose, a glucose molecule bonded to uridine diphosphate (UDP). This process is catalyzed by the enzyme galactose-1-phosphate uridyl transferase and transfers the UDP to the galactose molecule. The end result is UDP-galactose and glucose-1-phosphate. This process is continued to allow the proper glycolysis of galactose.

References

^ Carver, J.D. (2003). "Advances in nutritional modifications of infant formulas". The American Journal of Clinical Nutrition 77 (6): 1550S–1554S.
^ Thebody.com
^ Aseanfood.info
^ ^a ^b ^c Jonas DA, Elmadfa I, Engel KH, Heller KJ, Kozianowski G, König A, Müller D, Narbonne JF, Wackernagel W, Kleiner J (2001). "Safety considerations of DNA in food". Ann Nutr Metab 45 (6): 235–54. doi:10.1159/000046734. PMID 11786646.
^ Storck, R., 1965. Nucleotide Composition of Nucleic Acids of Fungi I. Ribonucleic Acids. J Bacteriol 90, 1260–1264.
^ Yamamoto T, Moriwaki Y, Takahashi S, Tsutsumi Z, Ka T, Fukuchi M, Hada T (October 2002). "Effect of beer on the plasma concentrations of uridine and purine bases". Metab Clin Exp 51 (10): 1317–23. doi:10.1053/meta.2002.34041. PMID 12370853.
^ Carlezon WA, Mague SD, Parow AM, Stoll AL, Cohen BM, Renshaw PF (February 2005). "Antidepressant-like effects of uridine and omega-3 fatty acids are potentiated by combined treatment in rats". Biol Psychiatry 57 (4): 343–50. doi:10.1016/j.biopsych.2004.11.038. PMID 15705349.
^ Stryer, Berg and Tymoczko (2002). "Section 16.1 Glycolysis Is an Energy-Conversion Pathway in Many Organisms". Biochemistry (5th ed.). New York: W H Freeman.

English Journal

2-thio-6-azauridine inhibits Vpu mediated BST-2 degradation.

Zhang Q1, Mi Z2,3, Huang Y4, Ma L5, Ding J6, Wang J7, Zhang Y8, Chen Y9, Zhou J10, Guo F11, Li X12, Cen S13.
Retrovirology.Retrovirology.2016 Mar 2;13:13. doi: 10.1186/s12977-016-0247-z.
BACKGROUD: BST-2 is an interferon-induced host restriction factor that inhibits the release of diverse mammalian enveloped viruses from infected cells by physically trapping the newly formed virions onto the host cell surface. Human Immunodeficiency Virus-1 (HIV-1) encodes an accessory protein Vpu t
PMID 26935098

Novel Nucleolipids of Pyrimidine β-D-Ribonucleosides: Combinatorial Synthesis, Spectroscopic Characterization, and Cytostatic/Cytotoxic Activities.

Knies C1, Hammerbacher K2, Bonaterra GA2, Kinscherf R2, Rosemeyer H3.
Chemistry & biodiversity.Chem Biodivers.2016 Feb;13(2):160-80. doi: 10.1002/cbdv.201500158.
Four series of nucleolipids with either uridine, 5-methyluridine, 5-fluorouridine, and 6-azauridine as β-D-ribonucleoside component have been prepared in a combinatorial (not parallel!) manner (see Formulae). All compounds have been characterized by elemental analyses, ESI mass spectrometry as well
PMID 26880429

Ameliorated or Acquired Cytostatic/Cytotoxic Properties of Nucleosides by Lipophilization.

Knies C1,2, Bonaterra G3, Hammerbacher K3, Cordes A3, Kinscherf R3, Rosemeyer H4.
Chemistry & biodiversity.Chem Biodivers.2015 Dec;12(12):1902-44. doi: 10.1002/cbdv.201500096.
A series of nucleolipids, containing one of the β-D-ribonucleosides 5-fluorouridine, 6-azauridine, uridine, or 5-methyluridine were lipophilized, either at the O-2',3'-position and/or at N(3) of the nucleobase with a large variety of hydrophobic residues. The resulting nucleolipids as well as the p
PMID 26663843

Japanese Journal

Synthesis of N^3-Substituted Uridine and Related Pyrimidine Nucleosides and Their Antinociceptive Effects in Mice

Shimizu Tomomi,Kimura Toshiyuki,Funahashi Tatsuya [他],WATANABE Kazuhito,HO Ing Kang,YAMAMOTO Ikuo
Chemical & pharmaceutical bulletin 53(3), 313-318, 2005-03-01
… Seventy eight N^3-substituted derivatives of uridine (1), thymidine (2), 2'-deoxyuridine (3), 6-azauridine (4), 2', 3'-O-isopropylideneuridine (5), and arabinofuranosyluracil (6) were synthesized and their antinociceptive effects were evaluated. …
NAID 10016652649

6-アザウラシルの抗コクシジウム活性の特徴

小林恒夫,針口二三男,岡本勉 [他],岡田之孝,林俊克,松野年美
The journal of veterinary medical science 58(2), 115-120, 1996-02-25
6-アザウラシル(AzU)の抗コクシジウム活性の特徴について調べるため, Eimeria tenella, E.necatrix, E.acervulina, E.maximaもしくはE.brunettiを感染した白色レグホーン雄ヒナを用いたバタリー試験を実施した. AzUは幼雛用基礎飼料に混合し, 供試ビナにオーシスト感染1日前から剖検時まで自由に摂取させた. AzUは, 飼料中1,000ppm …
NAID 110003916468

Central Nervous System Depressant Effects of N^3-Substituted Derivatives of Deoxyuridine in Mice

KIMURA Toshiyuki,KUZE Jiro,TERAOKA Seisaku,WATANABE Kazuhito,TATEOKA Yuji,KONDO Shigemi,HO IngKang,YAMAMOTO Ikuo
Biological & pharmaceutical bulletin 19(1), 142-145, 1996-01-15
… When the CNS depressant effects of phenacyl substituted 1 were compared to that of other oxopyrimidine nucleosides, N^3-phenacyluridine (13), N^3-phenacylthymidine (14), N^3-phenacyl-6-azauridine (15), compounds 12,13 and 14 (1.0 μmol/mouse, i.c.v.) significantly decreased mouse spontaneous activity. …
NAID 110003641076

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★リンクテーブル★

リンク元	「アザウリジン」
拡張検索	「6-azauridine triacetate」「6-azauridine」

「アザウリジン」

Uridine
	IUPAC name 1-[(3R,4S,5R)-3,4-dihydroxy-5-(hydroxymethyl)oxolan-2-yl]pyrimidine-2,4-dione
	Other names uridine
Identifiers
CAS number	58-96-8
ChemSpider	5807
UNII	WHI7HQ7H85
DrugBank	DB02745
MeSH	Uridine
ChEMBL	CHEMBL100259
Jmol-3D images	Image 1
	SMILES O=C1NC(=O)N(C=C1)[C@@H]2O[C@H](CO)[C@@H](O)[C@H]2O ;
	InChI InChI=1S/C9H12N2O6/c12-3-4-6(14)7(15)8(17-4)11-2-1-5(13)10-9(11)16/h1-2,4,6-8,12,14-15H,3H2,(H,10,13,16)/t4-,6-,7-,8-/m1/s1 ; Key: DRTQHJPVMGBUCF-XVFCMESISA-N InChI=1/C9H12N2O6/c12-3-4-6(14)7(15)8(17-4)11-2-1-5(13)10-9(11)16/h1-2,4,6-8,12,14-15H,3H2,(H,10,13,16)/t4-,6-,7-,8-/m1/s1; Key: DRTQHJPVMGBUCF-XVFCMESIBG ;
Properties
Molecular formula	C9H12N2O6
Molar mass	244.20 g mol−1
Appearance	solid
Density	.99308g/cm3
Melting point	167.2 °C (333.0 °F)
log P	-1.98
	Except where noted otherwise, data are given for materials in their standard state (at 25 °C (77 °F), 100 kPa)
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	Infobox references