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In the zona of stereochemistry, los structure of a compound and the three-dimensional arrangement of its atoms needs to be recognized to understand the behavioural and chemical properties of los compound. Whilst molecular entities are by their nature three-dimensional, lock are commonly depicted top top two-dimensional media. Therefore, ns certain level of distortion is essential to accurately convey los three-dimensional structure.

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In essential chemistry, there room conventions for depicting bonds within ns molecule. Un wedge-dash notation is provided to denote orientation of ns structure. Dotted present are used to represent an atomic bond i m sorry is additional away desde the viewer, un wedge for ns atoms nearer, and a solid línea to show a shortcut in plane with ns molecule.

Fischer and Haworth projections are dos types of illustration i m sorry are supplied to represent los 3D setup of atoms in carbohydrates. Castle are likewise used come compare various carbohydrates.

Fischer projections

The Fischer estimate was devised by alemán chemist Emil Fischer in 1891, who was the winner of los Nobel prize in Chemistry in 1902. In ns Fischer projection los carbohydrate is presented in its open chain form, fairly than ns cyclical one. Carbon atom in the main chain of ns carbohydrate molecule are associated vertically, whilst hydrogen atoms y hydroxyl teams are external inspection horizontally. Ns horizontal lines illustrate the bonds which come out of los page, conversely, the erigir lines admitir bonds that space in los page. Carbon atoms might or might not be presented in ns Fischer projection.


D-aldohexose sugars: allose, altrose, glucose, mannose, gulose, idose, galactose, talose. Fischer-like projections. Photo Credit: molekuul_be / Shutterstock

Fischer projections have actually one key advantage: that is simple to visually identify the stereochemical properties of un carbohydrate and compare the difference between dos carbohydrates quickly and easily. Because that example, that is sencillo to tell ns difference between dos enantiomers (molecules that are uno mirror photo of each other.)

A Fischer projection have the right to be rotated ciento ochenta degrees without affecting ns molecule’s stereoisomerism. If it were to be rotated 90 degrees then a different enantiomer would be illustrated, so because of this this is impossible with ns Fischer projection. Little changes deserve to affect ns molecule’s characteristics: therefore, care must be taken once using Fischer projections to illustrate uno carbohydrate.

As Fischer projections can have uno degree that ambiguity as soon as confused with other varieties of drawing, their use to stand for non-carbohydrates is discouraged. Castle are largely used to highlight monosaccharides. They have the right to be offered to represent various other organic molecules including amino acids, but this is discouraged by the 2006 IUPAC recommendations. IUPAC rules additionally determine that los hydrogen atoms have to be explicitly attracted especially ns hydrogen atoms of the end group of carbohydrates. Fischer projections are different to skeleton formulae.

Below is a Fischer projection of D-glucose in its open up chain form.

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Haworth projections

A Haworth forecast differs desde a Fischer forecast in the it is offered to represent ns carbohydrate in that is cyclical form. This is especially helpful for street which have uno ring structure. It to be devised by ns English chemist sir Norman Haworth who broadened on the work of Fischer, characterizing many more carbohydrates. He developed ns illustration technique after World battle 1, and received the mil novecientos treinta y siete Nobel Prize because that Chemistry because that his work in investigating carbohydrates y Vitamin C.

In uno Haworth projection, which is now los standard in necessary chemistry for stereochemical carbohydrate illustrations, more thick bonds in between carbon atoms represent those the next to los viewer, y the hydrogen/hydroxyl bond below ns plane of the carbon atoms stand for those on los right in a Fischer projection. However, this ascendancy does not use to los groups on ns two ring carbons bonded to los endocyclic oxygen atom.


D-aldohexose sugars: allose, altrose, glucose, mannose, gulose, idose, galactose, talose. Haworth-like projections. Image Credit: molekuul_be / Shutterstock

Compared to ns Fischer projection, wherein carbon atoms might or may not it is in illustrated, in un Haworth projection they room implied. Carbon uno is additionally referred to as the anomeric carbon. Hydrogen atom which space bonded to a carbon atom are additionally implied, so room not shown. Hydroxyl groups y other atom which might be bonded to los carbon ring space shown.

One drawback to Haworth projections is that they space not totally accurate in representing los spatial placing of all the atoms. Uno “chair” conformation deserve to be provided to an ext accurately depict ns spatial placing of the atoms; however, this conformation have the right to make decision of ns carbohydrate’s an easy stereochemistry more difficult.

Below is los Haworth estimate for los cyclic form of D-glucose.

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Choices between los Fischer and Haworth projections

As have the right to be seen, both Fischer and Haworth projections are two standard methods of illustrating the stereochemistry of uno carbohydrate. Whilst ns Haworth forecast is an ext commonly offered these days, and a chair conformation can assist to depict los atoms position in space, the Fischer projection definitely still has actually its uses in essential chemistry. Los choice between the two conventions is down to the distinta chemist.