2-DEOXYURIDINE (DEOXYRIBOSE URACIL)

2-DEOXYURIDINE
PRODUCT IDENTIFICATION
CAS NO.	951-78-0
EINECS NO.	213-455-7
FORMULA	C₉H₁₂N₂O₅
MOL WT.	228.20
H.S. CODE	2934.99.9000
TOXICITY
SYNONYMS	2'-Deoxyuridine; Deoxyribose uracil;
1-(2-Deoxy-beta-D-erythro-pentofuranoxyl)uracil; dURD;
Uracil desoxyuridine; Deoxyribose uracil; 2'-Desoxyuridine; (+)-2'-Deoxyuridine; 2'-Desoxyuridine; 1-(2-Deoxy-beta-D-erythro-ribofuranosyl)-2,4(1H,3H)-pyrimidinedione; 1-(2-Deoxy-beta-D-ribofuranosyl)-2,4(1H,3H)-pyrimidinedione;
SMILES	n1([C@@H]2O[C@H](CO)[C@H](C2)O)c([nH]c(=O)cc1)=O
CLASSIFICATION	Antimetabolite, Nucleoside Analog, Pyrimidinedione
EXTRA NOTES	An antimetabolite that is converted to deoxyuridine triphosphate during DNA synthesis. Laboratory suppression of deoxyuridine is used to diagnose megaloblastic anemias due to vitamin B12 and folate deficiencies. 2ĄĮ-Deoxyuridine (dU) is frequently halogenated to create thymidine analogues useful for studies of DNA synthesis and degradation mechanisms. Derivatized 2ĄĮ-Deoxyuridines used as labeling substrates include chloro-2ĄĮ-deoxyuridine (CldU), bromodeoxyuridine (BrdU) and/or iododeoxyuridine (IdU). Other useful analogues of 2ĄĮ-deoxyuridine include 5-ethynyl-2ĄĮ-deoxyuridine (DdU) and 5-hydroxymethyl-2ĄĮ-deoxyuridine (HmdU).
PHYSICAL AND CHEMICAL PROPERTIES
PHYSICAL STATE	white to off-white crystalline powder
MELTING POINT	163 - 167 C
BOILING POINT
SPECIFIC GRAVITY
SOLUBILITY IN WATER	300 g/l at 20 C
pH
VAPOR DENSITY
AUTOIGNITION
log P	-1.51E+00 (Octanol-water)
VAPOR PRESSURE	1.14E-13 (mmHg at 25 C)
HENRY LAW CONSTANT	7.72E-18 (atm-m3/mole at 25 C)
OH RATE CONSTANT	7.02E-11 (cm3/molecule-sec at 25 C Atmospheric)
NFPA RATINGS
REFRACTIVE INDEX
FLASH POINT
STABILITY	Stable under ordinary conditions
EXTERNAL LINKS & GENERAL DESCRIPTION
Wikipedia Linking Google Scholar Search Drug Information Portal (U.S. National Library of Medicine) - Deoxyuridine PubChem Compound Summary - Deoxyuridine Drug Bank - Deoxyuridine KEGG (Kyoto Encyclopedia of Genes and Genomes) - Deoxyuridine Local: Ribose is a pentose (five-carbon sugar) that is a component of the ribonucleic acid (RNA), where it alternates with phosphate groups to form the 'back-bone' of the RNA polymer and binds to nitrogenous bases. Ribose phosphates are components of the nucleotide coenzymes and are utilized by microorganisms in the synthesis of the amino acid histidine. Its close relative, deoxyribose, is a constituent of deoxyribonucleic acid (DNA), where it alternates with phosphate groups to form the 'back-bone' of the DNA polymer and binds to nitrogenous bases. The presence of deoxyribose instead of ribose is one difference between DNA and RNA. Ribose has one more oxygen atom in its molecule than deoxyribose. Ribose has a five member ring composed of four carbon atoms and one oxygen. Hydroxyl groups are attached to three of the carbons. The other carbon and a hydroxyl group are attached to one of the carbon atoms adjacent to the oxygen. In deoxyribose, the carbon furthest from the attached carbon is stripped of the oxygen atom in what would be a hydroxyl group in ribose. The sugar (ribose or deoxyribose) molecules in the nucleic acid are all oriented in the same direction. Their carbon atoms are numbered: the 5' carbon atom is always on the side of the sugar molecule that faces the leading end, while the 3' carbon atom always faces the tail end. Nucleotide is the structural unit of a nucleic acid. A nucleotide consists of either a nitrogenous heterocyclic base (purine or pyrimidine) , a pentose sugar (ribose or deoxyribose) and a phosphate group attached at the 5' position on the sugar. A nucleoside consists of only a pentose sugar linked to a purine or pyrimidine base, without a phosphate group. Purine bases are Adenine, Guanine and Hypoxanthine (examples of purine nucleosides are Adenosine, 2'-Deoxyadenosine, Guanosine, 2'-Deoxyguanosine, Inosine, 2'-Deoxyinosine). Pyrimidine bases are Cytosine, Thymine, and Uracil (examples of pyrimidine nucleosides are Cytidine, 2'-Deoxyguanosine, 5-Methyluridine, 2'-Deoxy-5-Methyluridine, Uridine, 2'-Deoxyuridine). The nucleoside derivatives are involved in important functions in cellular metabolism and are used to synthesize enzyme inhibitors, antiviral agents, and anticancer agents. Urasil is a pyrimidine base, occurring condensed with ribose or deoxyribose to form the nucleosides uridine and deoxyuridine in animal cells. It is a fundamental unit or base of nucleic acids. When N1 is linked to the C1 of ribose, urasil forms a pyrimidine nucleoside called uridines which are phosphorylated with from one to three phosphoric acid groups to form the three nucleotides; uridine monophosphate (UMP), uridine diphosphate (UDP), and uridine triphosphate (UTP) respectively. When N1 is linked to the C1 of deoxyribose, deoxy nucleosides and nucleotides are formed from urasil and deoxyribose; deoxyuridine monophosphate (dUMP), deoxyuridine diphosphate (dUDP), and deoxyuridine triphosphate (dUTP). UTP is an activated precursor in the synthesis of UDP-linked hexoses. UDP acts as the chief transferring coenzyme in carbohydrate metabolism to produce sucrose in plants, lactose and glycogen in mammals, and chitin in insects. UTP is involved in the formation of adenosine triphosphate (ATP) as a donator of phosphate groups to adenosine diphosphate (ADP). Uridine is important in biosynthesis of DNA and in the preservation and transfer of genetic information. It is known that there is no uridine in ribonucleic acid (RNA); the uridine nucleotides contain only deoxyribose. Urasil: a pyrimidine base Uridinea pyrimidine nucleoside Uridine Monophosphate (UMP, Uridylic acid): a nucleotide, the 5'-phosphate of uridine; a component of ribonucleic acid. Uridine Diphosphate (UDP): a nucleotide, the 5'-pyrophosphate of uridine; acting as the chief transferring coenzyme in carbohydrate metabolism; acting as a carrier of hexoses, hexosamines, and hexuronic acids which are intermediates in the metabolism. Uridine Triphosphate (UTP): a nucleotide, the 5'-triphosphate of uridine; acting as a precursor in the synthesis of ribonucleic acid and of UDP-linked intermediates. Deoxyuridine Monophosphate (dUMP): a nucleotide, the 5'-phosphate of deoxyuridine; an intermediate in the synthesis of deoxythymidine triphosphate. (deoxy-, also called desoxy, is a prefix for the designation of compounds which contain one less atom of oxygen than the reference substance). Deoxyuridine Diphosphate (dUDP): a nucleotide, the 5'-phosphate of deoxyuridine; an intermediate in the synthesis of deoxythymidine triphosphate. Deoxyuridine Triphosphate (dUTP): a nucleotide, the 5'-triphosphate of deoxyuridine; an intermediate in the synthesis of deoxyribonucleotides. Chemically modified nucleotides substituted or attached by special chemical groups or elements are studied and used to inactivate the normal biological operation in the living organism and the function of important enzymes.
SALES SPECIFICATION
APPEARANCE	fine off-white crystalline powder
ASSAY	97.0 - 102.0 %
OPTICAL ROTATION	+ 28º ~ +31 º
MELTING POINT	163 - 167 C
TRANSPORTATION
PACKING
HAZARD CLASS
UN NO.	Not regulated
SAFETY INFORMATION
Hazard Overview	Not known
EC DIRECTIVES
HAZARD CODES
RISK PHRASES
SAFETY PHRASES	24/25 Avoid contact with skin and eyes.
PRICE INFORMATION