Monosaccharides - N-Glycosides - Video Tutorials & Practice Problems
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Monosaccharides have the ability to react at the –O position in several different ways. In acidic conditions, monosaccharides can substitute selectively at the anomeric position to produce glycosides.
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General Reaction
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Hey, guys. Now let's talk about an oocyte reaction of mono sack rides called n like oxidation. So guys, mono sack rides have the ability to react at the O position or the oxygen position in several different ways. In acidic conditions, Monos actor rides can substitute selectively at the an America position on Lee at the an America position to produce what's known as Gleicher asides. Remember that Glick asides would put basically like in our group or some kind of substitute went over in the an America position. Okay, well, turns out that when nitrogenous, I'm just gonna put n for nitrogenous nuclear files, air used meaning nuclear files that get their lone pair or their nuclear Felicity from a nitrogen. That substitution product is called an end like aside. Okay, Because instead of forming an OGE like aside meaning that you have a like a side with an oxygen here instead, we're going to form a like acidic bond with a nitrogen containing compound. Okay, now, the term I'm gonna use most of the time for it is called an end like a side. So it's very similar toe OGE like a side, so it's very easy to remember. But another nomenclature term that you should just know. Is that end? Like, besides, air also referred to as like, causal means. Okay, So if you hear about Causal Amine or glad Casella mean, um, that is basically in a mean being attached to, uh, into a ring to a for notes or PIRA knows, and it means the same thing is ending like a side. Okay, So as you can see in this reaction that I'm about to show you, this molecule could either be named one amino d glucose piranha side. Because I'm saying that the, uh like a side is in amino group one amino. Or it could be referred to as d. Glueck, Opie Randall solo mean, because what we're saying is that it's the same as a glue cope IRA knows, except that it happens to having a mean in the an America position, which is a glide cost, which is a part Iran piranha, Sola mean. Okay, guys, I'm not gonna make You're not gonna be accountable for this nomenclature, but you should still recognize it. Okay, Awesome. So let's go through the general reaction. The general reaction says that if you take a cyclic carbohydrate, and then you react it with a nitrogen containing nuclear file. In this case, I'm using the simplest one, which is pneumonia. But it could have been a more complicated one in acid. What we're going to get is that the nitrogen attach it to the an American site and on Lee the an American site. And you're gonna get a mixture of Benin of animals with that nitrogen in the Glock acidic bond. This is called the End like acidic bond. Like go Sediq Link or bond. Okay, Um, I just wanna make some points here, so just you know, why can it on Lee react at the like at the an americ position and no other positions? Why would you Onley substitute the end here And not, for example, at C two guys for the same exact reason? Same exact mechanism as oh, glad consternation. Remember that. In order for oak like oxidation to take place, you need to pass through the Oxo Carbon iam Intermediate That stabilizes the positive charge right here. The same exact thing is gonna happen within like, oxidation where acid is going to come in, kick out the water I'm gonna form a double bond. And but all that happens within, like, oxidation. Is that it? The last step Nitrogen comes and attacks the positive charge here and then gets deep throat nated. And that is why we would get a nitrogen containing compounds. Looks very similar just at the America position. Cool. Awesome. So that is that so far in the next video, I'm gonna talk to you guys about specific types of end like besides that air called rival nuclear sites.
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Creating Ribonucleosides
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so in end, like a side that specifically contains a wry Bos mono sacha ride along with a heterocyclic nitrogen base, meaning it needs to be like an aromatic nitrogen containing hetero cycle. If you have those things connected through an end like acidic bond, which we just talked about that is actually referred to as a rival nucleoside or also just simplified to be called a nucleoside. Okay, now, keep in mind, it's a very different word than the one we had appear, not glide. Go side. Glide aside is this But if it's specifically a ribose with a heterocyclic nitrogen base, it's called a rival nuclear side, which happens to be guys the R and end portions of RNA RNA genetic material. Nucleic acids are actually just made out of a sugar backbone along with the nitrogenous base. So remember that RNA stands for ribonucleic acid, right? And what we're doing here is we're forming the rye bow and the nucleoside part. Okay, The only thing is that later on, they add phosphate groups. You add phosphate groups to get to the acid part. Okay, so how does this work? Well, first of all, guys, I'm gonna be showing you the four base pairs of RNA because, um, that's the easier one to talk about first. So you guys might remember this from biology. You may not remember this from biology, which is fine. I'm just gonna teach it from scratch, but basically the four heterocyclic basis that you could have for RNA. Argh! Wanting Sign a scene, Adami and yourself. And these are represented by the letters G. See A and you. Now, you might remember that there's a letter called T. You might be more familiar with tea, but T works with DNA, and it's very similar to you. Your assaults, like she just missing it has an extra metal group. That's it. But just knowing these bases, you pretty much have the big picture off. What a base looks like. Okay. And the way that RNA works the way that it's built is that you have a ribose sugar, remember? Ribose is all right. So we have d ribose and D ribose cycle eyes is to create Alfa d rival Farinos, which, um, it doesn't It doesn't always have to be Alfa Alfa happens to be the prevalent one for this one. Okay, So Alfa d rival Farinos by the By the way, the reason this one's Alfa is because notice that the stereo descriptor is facing up in this case because it's a d. So it's facing up. So then it Since it's Trans, that would be Alfa. Okay, Now, guys, what happens is you take that for a knows that rival for a nose and you attach it with an end like acidic bond to any one of these heterocyclic base is either guanine, cytosine, adenine or your soul. In fact, just you know, the nitrogen is that we would use would be these. It's either going to be this nitrogen for guanine and adenine, or it's gonna be this nitrogen for site, a scene in your soul. Okay, so these are the nitrogen specifically that attached to the an America position. And if you make that beta and linkage, what you're gonna wind up getting is what's called a rival nuclear side. In this case, right bows comes from the fact that it's a rival sugar nucleoside because it's now attached to a heterocyclic base. Okay, now, let's just break this down a little bit, So you guys know exactly what I'm talking about? Why did I call it a beta and linkage? Well, the end comes from the fact that it's an end like a site. Right? Where does the beta come from? Why is it beta? Because specifically, beta is the direction is the animal that faces cysts towards our, uh, stereo to Scripture. Right? Notice that my stereo descriptors facing up and this one's facing up and actually to be r n A. You need to be the beta animal. The Alfa animal doesn't work. It needs to be the beta animal. They need to both be facing up. So in this case, this rival night nuclear side is the basics of the base code. G g. Later on, all it needs is a phosphate group. Phosphate groups attached to the oh, and you're actually gonna have RNA. Okay. Specifically, it's called guano seen once you attach the rival sugar to Guan E. Isn't that cool? So, guys, even though this seems a little bit like a little bit advanced, like it seems like Oh, wow, we were just talking about sugar. And now I have, like a whole are on a molecule that I'm dealing with you guys know this whole mechanism. There's no reason that you can't build one of these from scratch now because we know how to use the an America position to make the oxy carbon iam ion that then could get attacked by the nitrogen. So, really, this is just a cool application of a mechanism you already know. All right, so let's go ahead and move on to the next video.
Note: The Adenine and Guanine structures should be switched.:)
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Problem
Problem
Propose an acid-catalyzed mechanism by which cytosine can form a β-1 N-linkage with 2-deoxy-β-Dribofuranose to produce a deoxynucleoside (DNA) called deoxycytidine.
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