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CURIOSITIES ABOUT GLUCCIDS

Welcome to a new entry. Muffins, bread, cakes ... they are very tasty, but did you know that they are made up of carbohydrates? Well, all this and much more in today's post.

Carbohydrates are organic biomolecules composed mainly of carbon, hydrogen and oxygen, although sometimes they can also have nitrogen, sulfur and phosphorus in their composition. The simplest are the osas or monosaccharides, which are made up of three to seven carbon atoms. A curiosity is that to detect a carbohydrate with reducing power, a test can be carried out in the laboratory. For this, Fehling's reagent is used, which is a solution of cupric sulfate in water and is blue in color. First, the reagent is added to the sugar solutions and, when oxidized, the aldehyde and ketone groups will form acid groups, thus giving up electrons that will be captured by the cupric inons. Later, when these cupric ions capture the electrons released earlier, they will form cuprous oxide, which is responsible for the red color of the precipitate. Therefore, we can deduce that this change from blue to red will determine whether there is the presence of carbohydrates or not.

 

On the other hand, to represent the cyclic structures of monosaccharides in a plane with their radicals at the top and bottom, the Haworth projection is used. The following photo shows how D-Glucose is cycled and is renamed α-D-glucopyranose. It is α because the -OH of the anomeric carbon, which is carbon 1, is below the plane, and ends in 'pyranose' because the carbon and oxygen atoms form a hexagonal structure. On the contrary, if the -OH of the anomeric carbon will remain above the plane it would be called β, and if a pentagonal structure were formed, as is the case of fructose, it would be called furanose. Finally, note that the formation of the cycle is carried out by a hemiacetal bond, which is a covalent bond between the aldehyde group and an alcohol and that occurs, for example, in cyclized glucose, or a hemicetallic bond between the ketone group and an alcohol such as that which takes place in fructose cyclization.

If you are not quite sure how to flip a cyclic molecule you can use the following trick. Take a cardboard or cardboard and draw the carbons and oxygen. Then, stick sticks in the carbons as a link, and finally, color the substituents with a marker or put balls in it as I have done. Now it only remains to turn it over to see how it would stay. I did it with D-fructose, but it can be done with any other cyclic molecule.

Fehling_edited.jpg

Source: Own image.

1602496984345_edited.jpg

Source: Own image.

Maqueta D-fructosa ciclada

Source: Own image.

As for the osides, if they are formed only by monosaccharides we will find the holsides, and if they also have other organic molecules in their composition we will speak of heterosides. It is easy to differentiate both types, since the prefix hetero- means 'distinct' and hol- 'all' or 'integer'. Returning to the topic, regarding the holsides, if they have more than ten bears, polysaccharides are formed, which in turn are divided into heteropolysaccharides and homopolysaccharides depending on whether they are composed of the same type of monosaccharides or more than one. If it only has two to ten bears, then we find the oligosaccharides, which if they are formed by the union of two bears, are called disaccharides. Furthermore, they are linked by O-glucosidic bonds established between two hydroxyl groups - (OH) of different monosaccharides. During the process, a water molecule is released, hence it is called dehydration synthesis.

It is worth highlighting the Iodine Test, whose purpose is to determine the presence of starch in a solution. The lugol reagent, which is a solution of iodine in distilled water, is added to the starch solution. The iodine molecules are introduced inside the amylose helix producing a blue optical effect. On the other hand, amylopectin forms much shorter helices, so the iodine molecules are unable to join and a yellowish color is obtained. The solution then turns purple and, if the starch concentration is high, it can go black.

1602500705845_edited.jpg

Source: Own image.

This reaction is the result of the formation of polyiodide chains from the reaction of starch with the iodine present in the solution of a reagent called Lugol. On heating the 'tinted' starch solution, it hydrolyzes and the iodine atoms leave them, thus the starch recovers its initial clear-yellowish color.

 

Finally, in the diagram you can finish seeing the function of each carbohydrate and the relationship of the different types of O-glucosidic bonds with the disaccharides.

 

See you in the next post. :-)

Esquema glúcidos

Source: Own image.

Information obtained from the unit and class notes.

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