LESSON 5: Cyclic forms of monosaccharides

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alpha (α) form - OH group on the first carbon atom projected downward
beta (β) form - OH group on the first carbon atom pointed upward

LESSON 6: Haworth projection formula

Here are some examples of monosaccharides presented in Haworth’s projection

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A: Pentose - a monosaccharide with five carbon atoms.
B: Hexose - a hexose is a monosaccharide with six carbons, but more specifically, an aldohexose is
a hexose with an aldehyde functional group at carbon number one.

LESSON 7: Reactions of Monosaccharides

Ester and Ether Formation
The -OH groups on a monosaccharide can be readily converted to esters and ethers.
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Glycoside Formation
Acetal derivatives formed when a monosaccharide reacts with an alcohol in the presence of an acid catalyst
are called glycosides.

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Biological Ester Formation: Phosphorylation
1) keeps them water soluble, and 2) prevents them from diffusing across lipid bilayer membranes. the
phosphorylation of alcohol groups is a critical metabolic step. In alcohol phosphorylations, ATP is almost
always the phosphate donor, and the mechanism is very consistent: the alcohol oxygen acts as a nucleophile,
attacking the gamma-phosphorus of ATP and expelling ADP (kennepohl, Reusch, & Farmer, 2020)

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Redox Reaction
The oxidation of the aldehyde group, one of the most easily oxidized organic functional groups. Aldehyde
oxidation can be accomplished with any mild oxidizing agent, such as Tollens' reagent or Benedict's reagent.

Chain Shortening and Lengthening

The chemical processes for decreasing or increasing the carbon chain length of glucose. Glucose can
be shortened by oxidation and decarboxylation to generate arabinose, a reaction known as the Ruff
degradation.

Wohl Degradation
The ability to shorten (degrade) an aldose chain by one carbon was an important tool in the structure
elucidation of carbohydrates. The following equation illustrates the application of this procedure to the
aldopentose, arabinose. Based on your knowledge of carbonyl chemistry, and considering that the Wohl
degradation is in essence the reverse of the Kiliani-Fischer synthesis.

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