Editing Monosaccharide (section)

===Open-chain stereoisomers===
Two monosaccharides with equivalent [[molecular graph]]s (same chain length and same carbonyl position) may still be distinct [[stereoisomer]]s, whose molecules differ in spatial orientation.  This happens only if the molecule contains a [[stereogenic center]], specifically a carbon atom that is [[chirality (chemistry)|chiral]] (connected to four distinct molecular sub-structures).  Those four bonds can have any of two configurations in space distinguished by their [[handedness]].  In a simple open-chain monosaccharide, every carbon is chiral except the first and the last atoms of the chain, and (in ketoses) the carbon with the keto group.

For example, the triketose H(CHOH)(C=O)(CHOH)H (glycerone, [[dihydroxyacetone]]) has no stereogenic center, and therefore exists as a single stereoisomer. The other triose, the aldose H(C=O)(CHOH)<sub>2</sub>H ([[glyceraldehyde]]), has one chiral carbon—the central one, number 2—which is bonded to groups −H, −OH, −C(OH)H<sub>2</sub>, and −(C=O)H. Therefore, it exists as two stereoisomers whose molecules are mirror images of each other (like a left and a right glove). Monosaccharides with four or more carbons may contain multiple chiral carbons, so they typically have more than two stereoisomers. The number of distinct stereoisomers with the same diagram is bounded by 2<sup>''c''</sup>, where ''c'' is the total number of chiral carbons.

The [[Fischer projection]] is a systematic way of drawing the [[skeletal formula]] of an acyclic monosaccharide so that the handedness of each chiral carbon is well specified.  Each stereoisomer of a simple open-chain monosaccharide can be identified by the positions (right or left) in the Fischer diagram of the chiral hydroxyls (the hydroxyls attached to the chiral carbons).

Most stereoisomers are themselves chiral (distinct from their mirror images).  In the Fischer projection, two mirror-image isomers differ by having the positions of all chiral hydroxyls reversed right-to-left. Mirror-image isomers are chemically identical in non-chiral environments, but usually have very different biochemical properties and occurrences in nature.

While most stereoisomers can be arranged in pairs of mirror-image forms, there are some non-chiral stereoisomers that are identical to their mirror images, in spite of having chiral centers.  This happens whenever the molecular graph is symmetrical, as in the 3-ketopentoses H(CHOH)<sub>2</sub>(CO)(CHOH)<sub>2</sub>H, and the two halves are mirror images of each other.  In that case, mirroring is equivalent to a half-turn rotation. For this reason, there are only three distinct 3-ketopentose stereoisomers, even though the molecule has two chiral carbons.

Distinct stereoisomers that are not mirror-images of each other usually have different chemical properties, even in non-chiral environments.  Therefore, each mirror pair and each non-chiral stereoisomer may be given a specific [[monosaccharide nomenclature|monosaccharide name]].  For example, there are 16 distinct aldohexose stereoisomers, but the name "glucose" means a specific pair of mirror-image aldohexoses. In the Fischer projection, one of the two glucose isomers has the hydroxyl at left on C3, and at right on C4 and C5; while the other isomer has the reversed pattern.  These specific monosaccharide names have conventional three-letter abbreviations, like "Glu" for glucose and "Thr" for [[threose]].

Generally, a monosaccharide with ''n'' asymmetrical carbons has 2<sup>''n''</sup> stereoisomers. The number of open chain stereoisomers for an aldose monosaccharide is larger by one than that of a ketose monosaccharide of the same length.  Every ketose will have 2<sup>(''n''−3)</sup> stereoisomers where ''n'' > 2 is the number of carbons.  Every aldose will have 2<sup>(''n''−2)</sup> stereoisomers where ''n'' > 2 is the number of carbons.
These are also referred to as epimers which have the different arrangement of −OH and −H groups at the asymmetric or chiral carbon atoms (this does not apply to those carbons having the carbonyl functional group).