Show the structure of a cerebroside made up of d-galactose, sphingosine, and myristic acid.

Question

Accepted Answer

Hi, everybody. Our next problem says, consider a cerebra side made up of D glucose, sphingosine and stric acid. And then in parentheses 18 to 0 or 18 colon zero, draw its structure. So let's recall that cerebro cys, we can see we're given three components here. And cerebro cys consist of a ceramide with a single sugar molecule attached at the one carbon hydroxyl position. And that a ceramide consists of a finger scene backbone plus a fatty acid. And we can see that in that we're told we have d glucose, there's our sugar sphingosine, our backbone and our fatty acid is stric acid. The 18 to 0 means it's 18 carbons with zero double bonds. So the best way to approach this is start with our finger scene backbone to remember that this Fingen is an 18 carbon amino alcohol that has an unsaturated hydrocarbon chain, unsaturated chain and kind of the most convenient way to draw it here. So we'll draw this vertical line as part of our finger scene. It's an amino alcohol with two alcohol groups. So I'm going to draw an oh group going up to the right there from that carbon. Then the next carbon down has an amino group. So there's NH two and then one more carbon that also has a hydroxyl group. There, there's our alcohol groups and our amino group. And then we know we need 18 carbons with one double bond there. So let's draw. So our top carbon here with that hydroxyl group on it, another carbon. So we're on to carbon 1234 and then between carbons four and five, we have that double bond. So we're on to five carbons with 18 total. So we need 13 more in our hydrocarbon chain. And I paused and drew that and came back because drawing a chain this long always involves lots of drawing, counting, recounting. Um always check twice in these long chains. It's very easy to lose track of your carbons. So there is my finger scene backbone. Now in my Samad portion, my fatty acid is going to be attached by an amid bond. So it will be attached to that amino group. So the fatty acid here. All right. And then the glucose will be attached to that hydroxyl group on the con carbon one. So glucose here note that the glucose is going to be attached by a beta glyco cytic bond. So our bond here to the oh group to that oxygen is going to go up when we attach it. So let's go ahead and attach our fatty acid which is stric acid with 18 carbons. And no double bonds. So we'll go ahead and erase why I wrote fatty acid here. Erase the two hydrogens right in my one hydrogen and then it's a fatty acid. So the first carbon hair will be a carbonyl group that's carbon one and then we need 17 more. So there's that long hydrophobic tail there. It of course, looks longer than this finger scene even though they have the same number of carbons because our fino backbone is wrapped around going down here. So we've got our ceramide portion, we just need to add our glucose. So we're going to draw it in a chair structure. As we said, we're going to have the bond to the oxygen there going up as a beta gly acidic bond, it's D glucose. So we know that the um carbon six will be above the plane of the ring. And by convention, we draw the oxygen within the ring, the back top right of that chair structure. So here is the bond to the carbon in the ring. Then go up to our oxygen, bringing the oxygen that goes over to carbon five. Let's finish drawing our chair here, excuse the sort of weird geometry. So to the left of our oxygen is our C H2O H carbon six with its hydroxyl group. Since this group is going up, the next one over to the left that oh group goes down, our next o age group goes up and then the next O A troop goes down noting that beco glyco beta glyco cytic bond is important because if we're just trying to glu glucose by itself that oh group in that place there on carbon one would be going down. But we have this bond here into this finger scene back backbone where it's going up to that oxygen there. So here is our cerebra side. We have our D glucose portion. We have our singo backbone with its alcohol and amid groups or amino group which has become an amid bond. The amid bond two are stric acid fatty acid chain. See you in the next video.

Show the structure of a cerebroside made up of d-galactose, sphingosine, and myristic acid.

Verified Solution

Key Concepts

Cerebrosides

Sphingosine

Fatty Acids