Derivatives of Monosaccharides - Video Tutorials & Practice Problems
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Derivatives of Monosaccharides
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In this video, we're going to begin our discussion on derivatives of monosaccharides. So recall that in our previous lesson videos, we mentioned that there are simple sugars in nature that have the exact formula here, cnh2o n, but there are also complex sugars in nature that can actually deviate from this exact formula. And so really these complex sugars are just derivatives of the simple sugars. And so we can call these monosaccharide derivatives or otherwise complex monosaccharides. Now, your professors and your textbooks, sometimes they'll say monosaccharide derivatives, other times they'll say complex monosaccharides And so now you guys know what they're referring to. And so really these monosaccharide derivatives or complex monosaccharides are just chemically modified monosaccharides. And so if they're chemically modified, that means that they can deviate from this exact formula here and so what we'll see is that these monosaccharide derivatives, they will take the hydroxyl groups of simple sugars and replace them with other chemical groups. Such as for instance, phosphate groups, carboxylic acids, or amino groups. And so when it comes down to it, really there are just 5 major groups of monosaccharide derivatives. And so you can see those 5 major groups down below in our image. And so the first is going to be sugar phosphates. The second is going to be sugar alcohols. The third is going to be deoxy sugars, the 4th is going to be amino sugars, and the 5th are going to be sugar acids. And so as we move forward in our course, we're going to talk about each of these 5 different groups of monosaccharide derivatives in their own separate videos. And so we'll start with the sugar phosphate so I'll see you guys in our next video
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Derivatives of Monosaccharides
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Alright. So, the first group of monosaccharide derivatives that we're going to talk about are the sugar phosphates. And so as you may have already guessed, sugar phosphates are just carbohydrates that are covalently attached to phosphate groups. And so as we'll see moving forward through our course, sugar phosphates are going to make up part of the structure of nucleotides. And of course, nucleotides make up the structure of nucleic acids such as for example DNA. And so notice down below we're showing you a DNA molecule and we're zooming in on this region of the DNA molecule here. And so you can see that we have these carbohydrates or these sugars, and notice that the sugars are covalently attached to phosphate groups. You can see that we have another sugar here that is also covalently attached to another phosphate group. And so it's true that the structure of DNA does include sugar phosphates. And later in our course, we'll talk more details about the exact structure of DNA but for now, we're focusing just on sugar phosphates. Now, you'll also note that later in our course when we're talking about carbohydrate metabolism, you'll find that sugar phosphates are going to be important intermediate in the pathways of both carbohydrate metabolism, and carbohydrate cuddabolism. And so this would be breaking things down and this would be building things up. And again, we'll talk more about this later in our course. But, if you take a look at this box over here, what you'll notice is that we've got this d glucose molecule here, which is a carbohydrate that, we can metabolize. And so notice that through phosphorylation, we can take the D glucose molecule and get a D glucose 6 phosphate molecule. And so notice that the d glucose, molecule is, now covalently attached to this phosphate group here. And so, we'll see many different intermediates in the pathways of carbohydrate metabolism and Catabolism that include these sugar phosphate. And so you can see this sugar phosphate, can continue through carbohydrate metabolism through the glycolysis pathway here. But again, we'll talk a lot more about carbohydrate metabolism later in our course and right now, we're just focusing on sugar phosphates. So they make up part of the structure of DNA and they're gonna be important, intermediates and carbohydrate metabolism and catabolism. So that concludes our introduction to sugar phosphates. And in our next video, we'll be able to talk about the next group of sugar derivatives which are the sugar alcohols. So I'll see you guys there.
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Derivatives of Monosaccharides
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Alright. So the next group of monosaccharide derivatives are the sugar alcohols, also known as aldotols. And so sugar alcohols or aldetols are just sugars whose carbonyl group is reduced to an alcohol group or an o h group. And so when this happens, every single carbon atom of the sugar is going to have its own alcohol group. And so usually, these sugar alcohols or aldotols are going to have the suffix itol added to the end of the name. And so if we take a look at our example of sugar alcohols down below right here, notice that we have the linear monosaccharide D glucose right here. And so through the process of reduction, we can reduce this aldehyde group into an alcohol group, an Oh group here. And we're also adding on this hydrogen atom right here. And so we're able to generate this molecule sorbitol which notice that when we look at every single one of its carbon atoms, they all have their own alcohol group and so that is also how we can easily identify sugar alcohols or aldotols and so that concludes our brief introduction to sugar alcohols and aldotols and I'll see you guys in our next video when we talk about the 3rd group of monosaccharide derivatives, deoxy sugars.
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Problem
Problem
What is the name of the sugar alcohol produced when D-ribose is reduced?
A
L-ribose.
B
D-ribitol.
C
D-ribulose.
D
L-ribitol.
E
L-ribulose.
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Derivatives of Monosaccharides
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Alright. So the 3rd group of monosaccharide derivatives that we're gonna cover are the deoxy sugars. Now, deoxy sugars are just going to be sugars that are missing at least 1 hydroxyl group and usually the hydroxyl groups are going to be missing usually due to the replacement with hydrogen atoms. And so a classic deoxy sugar is the sugar 2 deoxy d ribose. And so this prefix deoxy is used to indicate deoxy sugars. Now, 2 deoxy d ribose is the primary building block of DNA in all organisms and so later in our course when we focus our attention on nucleic acids and DNA structure, we will definitely revisit this idea of deoxy sugars. And so, if we take a look at our example down below, you can see the deoxy sugars in DNA. And so notice over here on the left, we have the fiorinos form of beta D ribose and so notice that this alcohol group on C 2. If it is replaced with a hydrogen atom or simply if we just remove the oxygen here, then what we can get, is, deoxyribose. And so we can convert beta d ribose into beta d two deoxyribose just by replacing the alcohol group, with a hydrogen atom on the c two carbon. And so this 2 right here is just telling us that it's the second carbon here that is going to have the alcohol replaced. And so this beta D2 deoxyribose here is the sugar that we see found in DNA. And so you can see that we have, DNA over here and, we're taking a zoom in of the DNA and, you can see that within, the structure of DNA that we do have this deoxy, beta D2 deoxyribose in there. And so this concludes our introduction to the deoxy sugars group of monosaccharide derivatives. And in our next lesson video, we'll talk about the 4th group of monosaccharide derivatives which are the amino sugar. So I'll see you guys there.
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Derivatives of Monosaccharides
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Alright. So the 4th group of monosaccharide derivatives that we're gonna talk about are the amino sugars. And so amino sugars are just sugars that are going to contain an amino group rather than containing a hydrox group at that position. And so as we'll see moving forward in our course, amino sugars are going to be commonly found in many oligosaccharides as well as polysaccharides. For example, chitin, which is a polysaccharide that we're gonna talk more about later in our course. And also these amino sugars, they're usually going to have the suffix amine. And so if we take a look at our example down below of amino sugars, notice that we're starting off with a beta D glucose molecule over here. And if we replace one of the hydroxyl groups here with an amino group, then, what we've got is a beta D glucosamine and notice that the ending has this suffix amine in it. And so, this concludes our introduction to amino sugars and in our next lesson video, we'll talk about the 5th and final group of monosaccharide derivatives, the sugar acids. So, I'll see you guys in that video.
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Derivatives of Monosaccharides
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Alright. So in this video, we're going to talk about the 5th and final class of monosaccharide derivatives, which are the sugar acids. And so, sugar acids are just carbohydrates with carboxylic acid groups and so really there are 3 main types of sugar acids that you guys should know and so the first type are the aldonic acids. The second type are the uronic acids, and the third type are the alderic acids. And so you'll notice that I intentionally capitalized the letter a in Aldonic, the letters u and r in Uronic, and the letters a and r in Alde Derek. And that's because we're gonna utilize this as a memory tool to help us distinguish between these three different, types of sugar acids. But before we introduce that memory tool, let's first go ahead and identify what each of these 3, sugar acids are. And so the aldonic acids are going to be aldoses who C one aldehyde group is oxidized into a carboxylic acid. And so aldonic acids usually have the suffix -onic. Now the next class, uronic acids, these are just sugars whose highest numbered carbon is oxidized into a carboxylic acid. And so, uronic acids usually have the suffix, uronic. And then, of course, last but not least, we have the alderic acids and so these are going to be sugars whose lowest and highest numbered carbons are oxidized to carboxylic acids. And so alderic acids are usually going to have the suffix, aric. And so, what you'll notice again, is we intentionally capitalize the letters that you see up above here. And so the A is the first letter of the alphabet and so that reminds us that aldonic acids are going to have their first carbon atom, the c one aldehyde, oxidized to a carboxylic acid. So you think first letter of the alphabet here with aldonic is the first carbon is oxidized. Now, uronic, we capitalize u and r, which are two letters that are towards the end of the alphabet. So they're closer to the end of the alphabet. And so this reminds us that it's the highest numbered or the carbon atoms towards the end of the sugars that are going to be, oxidized to carboxylic acids. And then notice that aldaric acid is, contains the letter a, which is the first letter of the alphabet, and the letter r, which is a letter towards the end of the alphabet. And so this reminds us that aldaric acids have both the lowest numbered carbon and the highest numbered carbon, oxidized to carboxylic acids. And so if we take a look at our example down below, we're going to label the following sugar acids. And notice over here on the far right in this box, we're starting on the left with a D glucose molecule. And notice that we have oxidation only at the c one carbon, the aldehyde group that's at the top, the c one aldehyde. And so it's being oxidized to a carboxylic acid. And so of course that is going to classify this because it's only the lowest numbered carbon. This is going to be an Aldonic acid. And of course, the prefix that or the suffix that it uses is onic. And so this is going to be gluconic acid. So we've converted d glucose into d gluconic acid. Now, in this next box over here, notice again we're starting with a d glucose molecule once again just like we started with d glucose over here. Except this time, notice that we have oxidation at the C 6 Carbon, which is the highest numbered carbon. And so the highest numbered carbon being oxidized to a carboxylic acid is going to be a uronic acid. And, what helps us remember that is again, the letters 'u' and 'r' are towards the end of the alphabet, and so this is at the end of, the sugar molecule here that's being oxidized and of course, the prefix that's typically used for uronic acid is just uronic. So this is going to be gluke d glucuronic acid. So we've converted d glucose into d glucuronic acid right here. And then last but not least over here in this last box, notice once again, we're starting with a d glucose molecule just like the previous 2. Except this time, notice that we have oxidation at both c one and c 6. So, we have oxidation at both ends at the lowest and the highest numbered carbons, being oxidized to carboxylic acids. And so again, because a alderic has the a and the r, that reminds us that it has the beginning and towards the end being oxidized. Again, the beginning and, towards the end being oxidized. So this is again going to be an alderic acid. And of course, the prefix or the suffix for alderic acid is just aric. And so this is going to be d glucaric acid. So we've converted d glucose into d glucaric acid. And so really that is it for our introduction to the sugar acids in the 3 types aldonic, uronic, and alderic. And we'll be able to get a little bit of practice with these concepts in our next video. So I'll see you guys there.
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Problem
Problem
Classify the following sugar acids as aldonic, uronic or aldaric acids: