Reducing and Non-reducing Sugars

Key Concepts Sugars exist in solution as an equilibrium mixture of open-chain and closed-ring (or cyclic) structures. In the open-chain form, the carbon atom that contains the C=O bond is called the carbonyl carbon. In the closed-ring (cyclic) structure, the carbonyl carbon is the one which is attached to the O of the ring and an OH group. Sugars that can be oxidised by mild oxidising agents are called reducing sugars because the oxidising agent is reduced in the reaction. A non-reducing sugar is not oxidised by mild oxidising agents. All common monosaccharides are reducing sugars. The disaccharides maltose and lactose are reducing sugars. The disaccharide sucrose is a non-reducing sugar. Common oxidising agents used to test for the presence of a reducing sugar are: a. b. c. Benedict's Solution Fehling's Solution Tollen's Reagent

Structure of Monosaccharides When the closed-ring (cyclic) structure of a monosaccharide opens to form a chain, the result may be either: an aldehyde (alkanal) a ketone (alkanone) O O || || or R- C -H R - C - R' Sugars that are aldehydes are known as aldoses. Sugars that are ketones are known as ketoses.

A monosaccharide containing 5 carbon atoms is known as a pentose. The open-chain form is therefore either: an aldopentose if it is an aldehyde (alkanal) or a ketopentose if it is a ketone (alkanone) A monosaccharide containing 6 carbon atoms is known as a hexose. The open-chain form is therefore either: an aldohexose if it is an aldehyde (alkanal) or a ketohexose if it is a ketone (alkanone)

Monosaccharide Glucose Fructose Closed-ring (cyclic) Structure Open-chain Structure Classification Testing for the Presence of a Reducing Sugar aldohexose ketohexose The common oxidising agents used to test for the presence of a reducing sugar: Oxidising Reagent Composition Colour of Solution Colour After Reaction with a Reducing Sugar Species Being Reduced (the oxidant) Species Being Oxidised (the reductant) Benedict's Solution copper sulfate in alkaline citrate deep blue brick red precipitate Cu2O(s) Cu2+ Cu 2+ Fehling's Solution copper sulfate in alkaline tartrate deep blue brick red precipitate Cu2O(s) Cu2+ + Tollen's Reagent silver nitrate in aqueous ammonia colourless silver mirror forms Ag(s) Ag+ + + e ---> Cu Cu 2+ + e ---> Cu Ag + e ---> Ag(s) + reducing sugar oxidised to carboxylate reducing sugar oxidised to carboxylate reducing sugar oxidised to carboxylate .

C -CH2OH ketose hydroxy carboxylate Oxidation Using Tollen's Reagent O || R.C .C -COO| H + Cu2O(s) brick red + 3H2O + 2Ag(NH3)2+ + 3OHcolourless O || R .Oxidation of Monosaccharides Oxidation of Aldoses Glucose and galactose are both examples of aldoses.C -COO| H OH | + 2Cu2+ + 5OHdeep blue R.C -CH2OH ketose hydroxy carboxylate OH | R.Ocarboxylate + 2Ag(s) silver mirror + 4NH3(g) + 2H2O O || R .Ocarboxylate + 2Cu2+ + 5OHdeep blue + Cu2O(s) brick red + 3H2O + 2Ag(NH3)2+ + 3OHcolourless + 2Ag(s) + 4NH3(g) + 2H2O silver mirror .C -H aldose Oxidation of Ketoses Fructose is an example of a ketose.C . Oxidation Using Benedict's or Fehling's Solution: O || R. Oxidation Using Benedict's or Fehling's Solution: O || R.C -H aldose Oxidation Using Tollen's Reagent O || R.

Structure and Oxidation of Disaccharides Sugar sucrose maltose lactose Cyclic Structure Glycosidic Link through Open-chain structure +Benedict's Solution +Fehling's Solution +Tollen's Reagent Type 2 carbonyl carbons no no reaction no reaction no reaction non-reducing sugar 1 carbonyl carbon yes forms brick red solid forms brick red solid forms silver mirror reducing sugar 1 carbonyl carbon yes forms brick red solid forms brick red solid forms silver mirror reducing sugar .

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