Definition
The term furanose denotes a five-component cyclic structure containing four carbon atoms and one oxygen atom and is generally reserved for the description of the molecular framework in monosaccharides. The furanose ring can be a cyclic hemiacetal of an aldopentose (e.g., ribose in RNA and deoxyribose in DNA) or a cyclic hemiketal of a ketohexose (e.g., fructose).
Overview
Furanose denotes a five-membered cyclic structure, belonging to a class of compounds termed carbohydrates, which are molecules composed of carbon, oxygen, and hydrogen with the empirical formula Cn(H2O)n. Furanoses are differentiated by various means, including the carbon framework from which hydroxyl groups are attached, the stereochemistry of the hydroxyl groups at each carbon (R or S), and the conformation of the overall structure (envelope or twist). Furanoses are either assigned a D- or L-configuration depending on the chirality of the stereocenter at the carbon farthest away from the aldehyde.
Furanose...
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References and Further Reading
Drew KN, Zajicek J, Bondo G, Bose B, Serianni AS (1998) 13C-labeled aldopentoses: detection and quantitation of cyclic and acyclic form by heteronuclear 1D and 2D NMR spectroscopy. Carbohydr Res 307:199–209
Eschenmoser A (1999) Chemical etiology of nucleic acid structure. Science 284:2118–2124
Eschenmoser A, Dobler M (1992) Why pentose and not hexose nucleic acids? Helv Chim Acta 75:218–259
Pitsch S, Wendeborn S, Krishnamurthy R, Eschenmoser A (2003) Pentopyranosyl oligonucleotide systems. 9th communication. Helv Chim Acta 86:4270–4363
Prieur B (2001) Étude de l’Activité Prébiotique Potentielle de l’Acide Borique. CR Acad Sci Ser II C Chem 4:667–670
Ricardo A, Carrigan M, Olcott N, Benner S (2004) Borate minerals stabilize ribose. Science 303:196
Sacerdote MG, Szostak JW (2005) Semipermeable lipid bilayers exhibit diastereoselectivity favoring ribose. Proc Natl Acad Sci U S A 102:6004–6008
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Krishnamurthy, R., Campbell, T., Kim, EK. (2014). Furanose. In: Amils, R., et al. Encyclopedia of Astrobiology. Springer, Berlin, Heidelberg. https://doi.org/10.1007/978-3-642-27833-4_607-4
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DOI: https://doi.org/10.1007/978-3-642-27833-4_607-4
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