Hydrolysis of both glycosidic bonds in the following trisaccharide A, B, C yields three monosaccharides.
c. Draw the Fischer projections for the three monosaccharides.

Question

Hydrolysis of both glycosidic bonds in the following trisaccharide A, B, C yields three monosaccharides.

c. Draw the Fischer projections for the three monosaccharides.

Accepted Answer

Welcome back, everyone. Three monosaccharide are formed when the trite shown below undergoes hydrolysis provide the facial projection of each monosaccharide. So essentially, during the hydrolysis reaction, we went to break the glyco cytic bonds. And essentially we're going to do that and we're going to consider the products. Now, what we want to do is simply add the O groups, right? So essentially when we break the first carbon oxygen bond, we just want to add hydroxy pointing down just as the six member implies. Because hydrogen is pointing up. Similarly, when we break the other carbon oxygen bond, we add o pointing down again for the second ring. Then when we break the other glyco cytic bonds, we're going to break one of the bonds to get O pointing up. And now for the other ring, we are breaking that bond and we can see that the O is pointing down and we end up with we structures we six membered rings. And because each of the sugars is a six membered ring and the anem carbon is at carbon number one, that's what we can see, right? The mono sac rights are Aldo heos. Since we have a total of six carbon atoms in each structure. So what we're going to do is simply draw a f projection in the very first carbon is going to be an aldehyde. Co when we consider the very first projection, we have to understand that if the o age group is pointing down on the rank, it will be on the right side of the fissure projection. So for example, o or the first ring is pointing down, right? So what we're going to do, we're, we're essentially going to consider that specific carbon which belongs to the aldehyde, right? So that's our C one position. And now when we look at C two and C three, those are the two coral positions. And we noticed that A H is pointing up, right? And if a wage is pointing up, it will be on the left side of the fure projection. So, oh, followed by, oh, and we have two hydrogens. The next carbon is carbon number four and oh is pointing down. If oh is pointing down, it will be on the right side of the fissure projection. Now, when we consider carbon number five, this is where we have to introduce an additional rule considering carbon number five, if carbon number six, that is bonded to carbon number five is pointing down and then it is an L sugar. So let's label the first one as L. The second one is D and the third one is D And if we have an L sugar, well, essentially, it means that oh is going to be on the left, right. So the final chiral position is going to have oh on the left, then we're going to add the missing hydrogens. And of course, C 512345 contains ch three at the very end of the chain. And we have our first Fisher projection and we can continue with the second one. Once again, it is an Aldo heos. So essentially we want to assign the appropriate subscriptions or atoms starting with co we noticed that we have oh, pointing up within the ring, right? Or carbon number two, meaning it is on the left followed by a wage pointing down. It is on the right followed by a wage pointing down. It is on the right. And now we have carbon number five, right. So carbon number five has hydrogen pointing down which is essentially opposite to the previous sugar. Now, if hydrogen is pointing down it, there's going to be on the left. And then because it is ad sugar, which is perfectly consistent with our analysis, we're going to have o on the right followed by carbon number six, which is in this case, CTO. Now let's add the remaining hydrogen atoms and let's continue with the next Fisher projection or the next Fisher projection. Once again, we're going to draw cho for carbon number one. Now let's consider carbon number two, Carpet number two has a wage pointing up and carbon number three has a wage pointing up which is very similar to the first structure. So those o are going to be on the left side of the Fisher projection and the remaining are the carbon hygen bonds. Considering the next carl position, we are going to look at carpet number four, which has a wage pointing down. If a wage is pointing down, we have a wage on the right and in this case, we have ad sugar, which means that oh, is on the right for the final chiral position followed by C H2O H which is carbon number six. And that's it. We have obtained the WE F projections. Thank you for watching.

Hydrolysis of both glycosidic bonds in the following trisaccharide A, B, C yields three monosaccharides.
c. Draw the Fischer projections for the three monosaccharides.

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Key Concepts

Glycosidic Bonds

Hydrolysis

Fischer Projections