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Fischer projection formulas of sugars

Pronunciation: fish'er

Definition: representations, by projection, of cyclic sugars, or derivatives thereof, in which the carbon chain is depicted vertically. The lowest-numbered asymmetric carbon atom (C-1 in aldoses; C-2 in 2-ketoses, fructose) is drawn at the top, and the rest of the carbon atoms of the chain are drawn in sequence below the top carbon atom. For each carbon atom, depicted in projection as lying in the plane of the paper, the carbon-to-carbon bond(s), which actually point away from the viewer, are drawn as vertical lines. The left-hand and right-hand bonds of each carbon atom, which actually point toward the viewer, are, in projection, depicted as horizontal lines. The conventions for the Fischer formulas of cyclic sugars are as follows: 1) If the highest-numbered asymmetric carbon atom has its OH (or its replacement) lying to the right, as is the 2-OH of d-glyceraldehyde, the sugar has the d configuration; if the OH is to the left, the sugar has the l configuration. 2) On the anomeric carbon atom (C-1 in the aldoses; C-2 in the 2-ketoses), an OH or substituted OH that lies to the right, with the OH of the highest-numbered asymmetric carbon atom also to the right, is defined to be a; if it is to the left, with the OH of the highest-numbered carbon atom still to the right, it is ß; the reverse applies if the latter OH is to the left. 3) The orientation of a terminal CH2OH group in the aldoses carries no configurational significance, as the group contains no asymmetric carbon atom.

[Emil Fischer]

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© Copyright 2017 Wolters Kluwer. All Rights Reserved. Review Date: Sep 19, 2016.