![]() ![]() If it is up like the butterflies, we have a beta isomer.īecause the hemiacetal carbon can adopt either of two configurations in a ring, it is given a special name. If it is down like the ants, we have an alpha isomer. If we have the Haworth projection, we can designate whether we have the alpha or beta from by seeing whether the hydroxy part of the hemiacetal points up or down. ![]() That means the ring oxygen in a Haworth projection is always found in the upper or upper right part of the drawing, with the hemiacetal carbon directly beside it to the right. In addition, we always keep the oxygen atom on the back edge of the ring (i.e. The hemiacetal carbon is always placed at the right edge of the drawing. However, in a Haworth projection, we have to orient the ring in a specific way. Remember, that's how we usually read a chair structure, too. The upper edge is read as being farther away. In a Haworth projection, the lower edge of the ring is read as being nearer to you. To distinguish these two designations, you need to look at the Haworth projection. In sugar chemistry, these two isomers are named a different way: alpha and beta. That means that two different stereochemical configurations can form at the hemiacetal carbon: R and S. There is nothing to distinguish one face from the other, and so approach from either face is equally likely. Because the carbonyl carbon is trigonal planar, the hydroxyl group can approach it from either face. When an open-chain sugar cyclizes by forming a hemiacetal, it forms a new stereocenter. Because there are many chiral canters in sugars, and becuase two sugars can differ by just one chiral center, Haworth projections make it easier to tell different sugars apart. In a Haworth projection, substituents are simply drawn straight up or straight down. In a diamond lattice projection, we have to keep track of whether a given substituent is in the upper or lower position at its particular site on the ring, and that requires careful attention. Instead, it tries to depict stereochemical relationships: whether two substituents are on the same face of the ring or opposite faces of the ring. A Haworth projection doesn't try to do that. The chair drawing or "diamond lattice projection" shows these relationships pretty well. Also, substituents on the atoms in the ring can be found above the ring, below the ring, or sticking out around the edge of the ring. The chair drawing shows that relationship, but in a Haworth projection, the ring is drawn as though it were flat. For example, in a six-membered ring, the atoms in the ring adopt a zig-zag, up-and-down pattern in order to optimize bond angles. The most common way of drawing these rings are in "Haworth projections." Haworth projections don't reflect the real shape of the ring. Five-membered rings are called "furanoses" and six-membered rings are called "pyranoses". ![]() As a result, five- and six-membered rings are very common in sugars. The hemiacetal forms when a hydroxyl group along the carbon chain reaches back and bonds to the electrophilic carbonyl carbon. That's because the carbonyl is usually "masked" as a hemiacetal. In fact, if you have seen drawings of sugars before, you might not have noticed the carbonyl. The OH at the anomeric carbon is on the same side as its CH 2OH group. They differ only in stereochemistry at C1 position, which is known as the anomeric carbon. Can a sugar react with itself? Of course. The two stereoisomers are interconverting structural isomers called anomers. In just one molecule, we have both an electrophile (the carbonyl) and a number of nucleophiles (the hydroxyls). This sort of structure presents lots of possibilities for reactions. In general, a sugar is a molecule that contains an aldehyde or a ketone, and every carbon other than the carbonyl carbon has a hydroxyl group attached to it. One strict definition of a carbohydrate is a polyhydroxylated aldehyde or ketone. The term "sugar" is often applied to any simple carbohydrate. L sugars will be shown with the hydrogen on the right and the hydroxyl on the left. They carry specialized chemical reagents into enzymes where reactions essential to life are carried out. On a Fischer projection of a monosaccharide, the penultimate ('next-to-last') carbon (alternatively, the last stereogenic carbon) of D sugars are depicted with hydrogen on the left and hydroxyl on the right. They aid in homebody security and defense operations by forming molecular codes on the surfaces of cells that identify whether the cell is one of our own or an intruder. ![]() For example, they lend structural support in the backbone of DNA. Although their best-known role is in energy storage in the form of glucose and starch, carbohydrates play a number of other roles. \)Ĭarbohydrates are an important class of biological molecules. ![]()
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