Common NameD-ribose
DescriptionD-Ribose, commonly referred to as simply ribose, is a five-carbon sugar found in all living cells. Ribose is not an essential nutrient because it can be synthesized by almost every tissue in the body from other substances, such as glucose. It is vital for life as a component of DNA, RNA, ATP, ADP, and AMP. In nature, small amounts of ribose can be found in ripe fruits and vegetables. Brewer's yeast, which has a high concentration of RNA, is another rich source of ribose. D-ribose is also a component of many so-called energy drinks and anti-ageing products available on the market today. Ribose is a structural component of ATP, which is the primary energy source for exercising muscle. The adenosine component is an adenine base attached to the five-carbon sugar ribose. ATP provides energy to working muscles by releasing a phosphate group, hence becoming ADP, which in turn may release a phosphate group, then becoming AMP. During intense muscular activity, the total amount of ATP available is quickly depleted. In an effort to correct this imbalance, AMP is broken down in the muscle and secreted from the cell. Once the breakdown products of AMP are released from the cell, the energy potential (TAN pool) of the muscle is reduced and ATP must then be reformed using ribose. Ribose helps restore the level of adenine nucleotides by bypassing the rate-limiting step in the de novo (oxidative pentose phosphate) pathway, which regenerates phosphoribosyl pyrophosphate (PRPP), the essential precursor for ATP. If ribose is not readily available to a cell, glucose may be converted to ribose. Ribose supplementation has been shown to increase the rate of ATP resynthesis following intense exercise. The use of ribose in men with severe coronary artery disease resulted in improved exercise tolerance. Hence, there is interest in the potential of ribose supplements to boost muscular performance in athletic activities (PMID: 17618002 , Curr Sports Med Rep. 2007 Jul;6(4):254-7.).
Structure
Molecular FormulaC5H10O5
Average Mass150.12990
Monoisotopic Mass150.05282
IUPAC Name(3R,4S,5R)-5-(hydroxymethyl)oxolane-2,3,4-triol
Traditional NameD-ribofuranose
CAS Registry Number613-83-2
SMILESOC[C@H]1OC(O)[C@H](O)[C@@H]1O
InChI IdentifierInChI=1S/C5H10O5/c6-1-2-3(7)4(8)5(9)10-2/h2-9H,1H2/t2-,3-,4-,5?/m1/s1
InChI KeyHMFHBZSHGGEWLO-SOOFDHNKSA-N
CHEBI IDCHEBI:47013
HMDB IDHMDB0000283
Pathways
NameSMPDB/PathBank
pentose phosphate pathway
Glucose-6-phosphate dehydrogenase deficiency
Ribose-5-phosphate isomerase deficiency
Transaldolase deficiency
StateSolid
Water Solubility1.07e+03 g/l
logP-2.65
logS0.85
pKa (Strongest Acidic)11.31
pKa (Strongest Basic)-2.98
Hydrogen Acceptor Count5
Hydrogen Donor Count4
Polar Surface Area90.15 Ų
Rotatable Bond Count1
Physiological Charge0
Formal Charge0
Refractivity29.96 m³·mol⁻¹
Polarizability13.68

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