Biochemistry Online: An Approach Based on Chemical Logic

CHAPTER 3 - CARBOHYDRATES/GLYCANS

A: Mono- and Disaccharides

03/14/16

Learning Goals/Objectives for Chapter 3A: After class and this reading, students will be able to

define a sugar
apply knowledge about reactions at carbonyl carbons of aldehyde and ketones in the formation of hemiacetals/hemiketals and acetals/ketals from organic chemistry to draw mechanics showing cyclization of aldoses and ketoses and (hemiacetal/hemiketal formation) and of polymerization of aldoses and ketones to form dissacharide and polysaccharide (acetal/ketals).
draw open chain, Haworth (planar), and puckered (nonplanar) representations of 6 member cyclic sugars
know the names of common trioses, ribose (5C) and hexoses and draw open chain, Haworth, and puckered representations of each
differentiate between enantiomers, diastereomers and anomers of the hexoses
explain the difference between reducing and nonreducing dissacharides
draw the structure and name common sugar derivatives of the hexoses

The link below is an extraordinary and free resource on glycobiology. It defines the word "glycan" as a "generic term for any sugar or assembly of sugars, in free form or attached to another molecule" and "is used interchangeably ... with saccharide or carbohydrate."

Essentials of Glycobiology, 2nd edition, is available online.

A5. Recent Links and References

3-D interactive structures of Biological molecules - Jsmol structures for monosaccharides (top)
glycosidase classification
CHO nomenclature - IUPAC/IUBMB
Glycan structural database
Consortium for function glycomics molecules

Byres, E. et al. Incorporation of a non-human glycan mediates human susceptibility to a bacterial toxin. Nature 456, 648-652 (2008)
Pam Tangvoranuntakul, Pascal Gagneux, Sandra Diaz, Sandra Diaz, Ajit Varki, and Elaine Muchmore

and Elaine Muchmore. Human uptake and incorporation of an immunogenic nonhuman dietary sialic acid. PNAS 2003 100:12045-12050
Cramer and Truhlar. Quantum Chemical Conformational Analysis of Glucose in Aqueous solutions. J. Am. Chem. Soc. 115, pg 5745 (1993)

back Navigation

Return to Chapter 3A: Monosaccharide Sections

Return to Biochemistry Online Table of Contents

Archived version of full Chapter 3A: Mono- and Disaccharides

Biochemistry Online by Henry Jakubowski is licensed under a Creative Commons Attribution-NonCommercial 4.0 International License.