Pentoses
A pentose is a monosaccharide with five carbon atoms. Pentoses are organized into two groups. Aldopentoses have an aldehyde functional group at position 1. Ketopentoses have a ketone functional group at position 2 or 3. in the cell, have a higher metabolic stability than hexoses
The aldopentoses have three chiral centers and therefore eight (23) different stereoisomers are possible.
Ribose is a constituent of RNA, and the related molecule, deoxyribose, is a constituent of DNA. Phosphorylated pentoses are important products of the pentose phosphate pathway, most importantly ribose 5-phosphate (R5P), used in the synthesis of nucleotides and nucleic acids, and erythrose 4-phosphate (E4P) used in the synthesis of aromatic amino acids.
The 2-ketopentoses have two chiral centers, and therefore four (23) different stereoisomers are possible. The 3-ketopentoses are rare.
The aldehyde and ketone functional groups in these carbohydrates react with neighbouring hydroxyl functional groups to form intramolecular hemiacetals and hemiketals, respectively. The resulting ring structure is related to furan, and is termed a furanose. The ring spontaneously opens and closes, allowing rotation to occur about the bond between the carbonyl group and the neighbouring carbon atom — yielding two distinct configurations (α and β). This process is termed mutarotation.
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