Biochemistry Online: An Approach Based on Chemical Logic

Biochemistry Online


A:  Mono- and Disaccharides


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."


A5.  Recent Links and References


  1. Byres, E. et al.  Incorporation of a non-human glycan mediates human susceptibility to a bacterial toxin.  Nature 456, 648-652 (2008)

  2. 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

  3. Cramer and Truhlar.  Quantum Chemical Conformational Analysis of Glucose in Aqueous solutions. J. Am. Chem. Soc.  115, pg 5745 (1993)


Return to Chapter 3A:  Monosaccharide Sections

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


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