Deoxyribosides

Cytosine was isolated from hydrolysis of calf thymus in 1894 and by 1903 its structure was known and it had been synthesized from 2-ethylthiopyrimidin-4(3H)-one. The acid hydrolysis of ribonucleic acid gives nucleotides, among which are two cytidylic acids, 2 -and 3 -phosphates of cytidine further hydrolysis gives cytidine itself, i.e. the 1-/3-D-ribofuranoside of cytosine, and thence cytosine. The deoxyribonucleic acids likewise yield deoxyribonucleotides, including cytosine deoxyribose-5 -phosphate, from which the phosphate may be removed to give cytosine deoxyriboside and thence cytosine. 

The first chemical synthesis of these substances, using a procedure which yields 1-ribofuranosyl derivatives by pyrimidine bases, was described by Hall. By using the mercuric salt of 6-azathymine and tribenzoate of D-ribofuranosyl chloride, he obtained a mixture of two monoribosyl derivatives and a diribosyl derivative. He determined the structure of the 3-substituted derivative by the similarity of spectra and other properties to those of 3-methyl-6-razauracil. The structure of the 1-ribosyl derivative was then determined from the similarity of the spectra with 6-azathymine deoxyriboside obtained enzymatically. 

Deoxy-p-D-eryfhro-pentofuranosyl)adenine not adenine 8-(2-deoxyriboside) o... 

Laland SG, Serck-Hanssen G (1964) Synthesis of pyrimidin-2-one deoxyribosides and their ability to support die growth of the deoxyriboside-requiring organism lactobacillus acidophilus r26. Biochem J 90 76-81... 

Gao J, Strassler C, Tahmassebi D, Kool ET (2002) Libraries of composite polyfluors built from fluorescent deoxyribosides. J Am Chem Soc 124 11590-11591... 

The deoxyriboside derivative of 5-methylaminouracil (LlVa) is a specific antiherpes agent [399]. The aglycone itself (LIVb) as well as 5-aminouracil, however, has no antiviral activity [399]. 

The most important pyrimidine derivatives are those upon which biological organisms depend. Cytosine 1018 and uracil 1019 are found in ribonucleic acid (RNA) in the form of their ribonucleotides, cytidine 1020 and uridine 1021, while in deoxyribonucleic acid (DNA), cytosine and thymine 1022 are found in the form of their 2 -deoxyribonucleotides, 2 -deoxycytidine 1023 and thymidine 1024. 5-Methylcytosine 1025 is also found to a small extent (c. 5%) in human DNA in the form of its 2 -deoxyriboside 1026, and 5-(hydroxymethyl)cytosine-2 -deoxyriboside 1027 has also been detected in smaller amounts <2005CBI1>. Many variants of cytosine and uracil can be found in RNA including orotic acid 1028 in the form of its ribonucleotide orotidine 1029. Other pyrimidine derivatives to have been isolated from various biological sources include 2 -deoxyuridine 1030, alloxan 1031, and toxopyrimidine (pyramine) 1032 (Figure 2). 

Extending this experiment to DNA relies on a coumarin-102 deoxyriboside as a base-pair replacement [10]. Standard oligonucleotide synthesis techniques allow this probe to be placed into a DNA strand of any desired sequence. The TRSS experiment becomes sensitive to the time-dependent polarity experienced in the interior of the DNA. The polarity may have contributions from the movement of any of the charged groups intrinsic to the structure, such as the full charges on the backbone phosphates, the partial charges of the base pair heteroatoms, or the surrounding water and counterions. 

Esterification of the 5 -hydroxyl group of deoxyribose nucleosides, such as cytosine deoxyriboside, with phosphoric acid gives the corresponding... 

Deoxyribosides, but not ribosides, of 2-fluoro-, 2-bromo- and 2-chloroadenine are cytotoxic and effective against a leukemia LI 10 system133. 

The 5-chloro, 5-bromo and 5-iodo derivatives of uracil are base analogues of thymine and, in cellular systems, can replace the latter in DNA u >. Furthermore, 5-iodo-2 -deoxyuridine is an antiherpes agent currently used for treatment of ocular herpes keratitis. By contrast, 5-fluorouracil can replace uracil in RNA, and, together with 5-fluoro-2 -deoxyuridine, is employed in tumour chemotherapy. All the foregoing are also known mutagens, and 5-bromouracil and its deoxyriboside are widely employed in studies on mutagenesis U9). 

SYNS BDU 5-BDU BROMODEOXYURIDINE 5-BROMODEOXYURIDINE 5-BROMO-2-DEOXYURIDINE 5-BROMODESOXYURIDINE BROMOURACILDEOXYRIBOSIDE 5-BROMOURACIL DEOXYRIBOSIDE 5-BROMOURACIL-2-DEOXYRIBOSIDE BROXURIDINE BRUDR BUDR 5-BUDR... 

SYNS CYTOSINE DEOXYRIBOSIDE dCYD 2 -DEOXYCYTIDINE DEOXYRIBONUCLEOSIDE CYTOSINE O DEOXYRIBOSE CYTIDINE DESOXYCYTIDIN (GERMAN)... 

SYNS DEOXYFLUOROURIDINE l-p-d-2 -DEOXYRIBOFURANOSYL-5-FLUOROURACIL FDUR FLOXURIDIN FLOXURIDINE FLUORODEOXY-URIDINE p-5-FLUORO-2 -DEOXYURIDINE 5-FLUORODEOXYURIDINE 5-FLUORO-2-DEOXY-URIDINE 5-FLUORO-2 -DEOXYURIDINE 5-FLUOROURACIL DEOXYRIBOSIDE 5-FLUORO-URACIL-2 -DE0XYRIB0SIDE FLUORURIDINE DEOXYRIBOSE FUDR 5-FUDR NSC-27640 RO 5-0360... 

SYNS ALLERGAN 211 DENDRID l-(2-DEOXY-P-d-RIBOFURANOSYL)-5-IODOURACIL l-P-d-2 -DEOXYRIBOFURANOSYL-5-IODOURACIL EMANIL HERPESIL HERPIDU HERPLEX HERPLEX LIQUIFILM IDEXUR IDOXENE IDOXURIDIN IDOXURIDINE IDU IDUCHER IDULEA IDUOCULOS IDUR IDURIDIN 5-IODODE-OXYURIDINE 5-IODO-2 -DEOXYURIDINE 5-lODOURACIL DEOXYRIBOSIDE lUDR 5-IUDR JODDEOXIURIDIN KERECID NSC-39661 OPHTHALMADINE SKStF 14287 STOXIL SYNMIOL... 

SYNS DEOXYTHYMIDINE 2 -DEOXYTHYMIDINE DT DTHYD 5-METHYLDEOXYURIDINE THYMIDIN THYMINEDEOXYRIBOSIDE THYM-INE-2-DEOXYRIBOSIDE... 

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