Interdisciplinary Note (8 of 29)
Glucose ring formation
Glucose ring formation.

Hemiacetal formation is the mechanism by which pentoses and hexoses assume their cyclic forms. Nucleophilic attack by typically the #4 or #5 carbon's hydroxyl group onto the carbonyl group (the anomeric carbon) of the noncyclic form leads to hemiacetal formation. Another nucleophile can act out the second part of the acetal formation mechanism upon the anomeric carbon forming a mixed acetal, termed a glycoside. The nucleophile may be adenine, guanine, cytosine, thymine, or uracil, in which case the glycoside product is a nucleoside, a fundamental building block of the nucleic acids DNA and RNA. If the nucleophile is another sugar, the process leads to the formation of a disaccharide (or polysaccharide). In other words, disaccharides are glycosides with the nucleophile being another sugar molecule.

The Integrated MCAT Course is a trademark of Wisebridge Learning Systems. Unless otherwise specified, the works of the Integrated Course are published under a Creative Commons Attribution NonCommercial ShareAlike License. MCAT is a registered trademark of the Association of American Medical Colleges, which does not endorse the Integrated MCAT Course. The Integrated MCAT Course offers our customers no guarantees regarding eventual performance on the MCAT.