Ribose


Ribose
D-Ribose
Identifiers
CAS number 50-69-1 YesY
PubChem 5779
EC-number 200-059-4
DrugBank DB01936
ChEMBL CHEMBL1159662 N
Properties[1][2]
Molecular formula C5H10O5
Molar mass 150.13 g/mol
Appearance white solid
Melting point

95 °C, 368 K, 203 °F

Solubility in water very soluble
Chiral rotation [α]D −21.5º (H2O)
Related compounds
Related aldopentoses Arabinose
Xylose
Lyxose
Related compounds Deoxyribose
 N (verify) (what is: YesY/N?)
Except where noted otherwise, data are given for materials in their standard state (at 25 °C, 100 kPa)
Infobox references

Ribose is an organic compound with the formula C5H10O5; specifically, a monosaccharide (simple sugar) with linear form H–(C=O)–(CHOH)4–H, which has all the hydroxyl groups on the same side in the Fischer projection.

The term may refer to any of two enantiomers: almost always to D-ribose, which occurs widely in nature and is discussed here; or to its synthetic mirror image L-ribose, which is not found in nature and is of limited interest.

D-Ribose was first reported in 1891 by Emil Fischer. It is a C'-2 carbon enantiomer of the sugar D-arabinose (both isomers of which are named for their source, gum arabic) and ribose itself is named as a transposition of the name of arabinose.[3]

Ribose comprises the backbone of RNA, a biopolymer that is the basis of genetic transcription. It is related to deoxyribose, as found in DNA. Once phosphorylated, ribose can become a subunit of ATP, NADH, and several other compounds that are critical to metabolism like the secondary messengers cAMP and cGMP.

Structure

Ribose is an aldopentose, that is a monosaccharide containing five carbon atoms that, in its open chain form, has an aldehyde functional group at one end. In the conventional numbering scheme for monosaccharides, the carbon atoms are numbered from C1' (in the aldehyde group) to C5'. The deoxyribose derivative, found in DNA, differs from ribose by having a hydrogen atom in place of the hydroxyl group in carbon C2'.

Like many monosaccharides, ribose occurs in water as the linear form H–(C=O)–(CHOH)4–H and any of two ring forms: ribofuranose ("C3'-endo"), with a five-membered ring, and ribopyranose ("C2'-endo"), with a six-membered ring. The ribofuranose form is predominant in aqueous solution.

The "D-" in the name D-ribose refers to the stereochemistry of the chiral carbon atom farthest away from the aldehyde group (C4'). In D-ribose, as in all D-sugars, this carbon atom has the same configuration as in D-glyceraldehyde.

Phosphorylation

In biology, D-ribose must be phosphorylated by the cell before it can be used. Ribokinase catalyzes this reaction by converting D-ribose to D-ribose 5-phosphate. Once converted, D-ribose-5-phosphate is available for the manufacturing of the amino acids tryptophan and histidine, or for use in the pentose phosphate pathway. The absorption of D-ribose is 88–100% in the small intestines (up to 200 mg/kg/hr).[4]

References

  1. ^ The Merck Index: An Encyclopedia of Chemicals, Drugs, and Biologicals (11th ed.), Merck, 1989, ISBN 091191028X , 8205.
  2. ^ Weast, Robert C., ed (1981). CRC Handbook of Chemistry and Physics (62nd ed.). Boca Raton, FL: CRC Press. p. C-506. ISBN 0-8493-0462-8. .
  3. ^ Nechamkin, Howard (1958). "Some interesting etymological derivations of chemical terminology". Science Education 42: 463. doi:10.1002/sce.3730420523. 
  4. ^ [1][dead link]

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Look at other dictionaries:

  • Ribose — Structure du D ribose et du L ribose Général Nom IUPAC (2R,3S,4R) 5 (Hydroxymethyl) tetrahydrofuran …   Wikipédia en Français

  • ribose — [ riboz ] n. m. • 1932; de acide ribonique, de arabinose « principe soluble de la gomme arabique », et 1. ose ♦ Biochim. Ose de formule C5H10O5, présent dans l acide ribonucléique. La forme réduite du ribose est le désoxyribose. ● ribose nom… …   Encyclopédie Universelle

  • ribose — 1892, from Ger. Ribose (1891), shortened and arbitrarily rearranged from English arabinose (c.1880), a sugar which is so called because it is formed from gum arabic …   Etymology dictionary

  • ribose — s. f. [Química] Pentose que entra na composição de ácidos nucleicos.   ‣ Etimologia: alemão Ribose …   Dicionário da Língua Portuguesa

  • ribose — ribose. См. рибоза. (Источник: «Англо русский толковый словарь генетических терминов». Арефьев В.А., Лисовенко Л.А., Москва: Изд во ВНИРО, 1995 г.) …   Молекулярная биология и генетика. Толковый словарь.

  • ribose — [rī′bōs΄] n. [< Ger rib(onsäure), a tetra hydroxy acid, arbitrarily altered < arabinose,ARABINOSE + säure, acid + OSE1] a pentose sugar, C5H10O5, that is a basic component of RNA, riboflavin, etc …   English World dictionary

  • Ribose — Strukturformel offenkettige Darstellung in der Fischer Projektion Allgemeines …   Deutsch Wikipedia

  • ribose — /ruy bohs/, n. Biochem. a white, crystalline, water soluble, slightly sweet solid, C5H10O5, a pentose sugar obtained by the hydrolysis of RNA. [1890 95; < G Ribose, earlier Ribonsäure, equiv. to Ribon (from Arabinose ARABINOSE, by arbitrary… …   Universalium

  • Ribose — Ri|bo|se 〈f. 19; Biochem.〉 Zuckerart mit fünf Sauerstoffatomen, wichtiger Bestandteil der Nukleinsäuren [durch Buchstabenvertauschung zu rib..., ribo... <Arabin „fester Bestandteil des Gummiarabikums“] * * * Ri|bo|se, hier D Ribose [aus… …   Universal-Lexikon

  • ribose — Pentose Pen tose, n. [Penta + ose.] (Chem.) Any of a group of sugars of the formula {C5H10O5}, such as as {arabinose} or {ribose}; so called from the five carbon atoms in the molecule. They are not fermented by yeast. [Webster 1913 Suppl.] …   The Collaborative International Dictionary of English


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