Chemistry Lesson Plan

 

Limiting reagents cause focused attention in dark brown, hazel, and blue eyes

 Laws of thermodynamics gather shades of brown, olive, yellow, tan, and white

 Oxidation number rules are quickly, carefully transcribed

 By Papermate pencils tightly gripped by fingernail-chewed hands,

 How do I convince them that they are brilliant

 That they shine when they solve, explain, and share with each other

 How do I help them decimate their low confidence and troubling anxieties

 Their capabilities extend as far as they can see themselves where they want to be

 How do I lure them into believing they are diamonds in the rough

 Not walking wounded

 But able-bodied, neuroplastic, thermodynamic, electo-kinetic, spontaneous

 Emissions of power, knowledge, and potential

A Healthier French Fry? Simplot Says So

How many of us have munched on a plate of fries or chips and wondered about the health consequences? Recently, giant potato company Simplot has generated a potato that contains less of an amino acid that leads to a potential carcinogen called acrylamide. 

Image of fries from http://www.simplotfoods.com/Recipe/18433

Acrylamide (right) has amide and alkene functional groups.

What is this amino acid that causes concern? It is asparagine and is

found to be of highest concentration in french fries and in smaller amounts in baked goods, batter-fried fish and chicken, and even in coffee powder and beer.

From a food safety report about the health implications of acrylamide.

http://www.who.int/foodsafety/publications/acrylamide-food/en/

Asparagine is an amino acid which can change during high temperature cooking into a potential carcinogen acrylamide. Chiral center, carboxylic acid, and amine functional groups are highlighted.

According to a 2007 report from the U.S. Food and Drug Admin-istration, acrylamide typically found in commercial applications such as packaging and in scientific research. Its appearance in food comes from high-temperature cooking such as baking, roasting, and frying where the Maillard Reaction converts naturally occurring asparagine into acrylamide. This often occurs in the presence of sugars found in foods. Acrylamide has been detected in plant-based foods, such as French fries and potato chips. It has also been found in cookies, crackers, breakfast cereals, and bread. The FDA esti- mates that the average amount of acrylamide ingested each day is 0.4 microgram/kilogram of body weight.

In a paper by C.M. Rommens, H. Yan, K. Swords, C. Richael, and J. Ye published in Plant Biotechnology Journal, they were able to create a potato with a lower amount of asparagine by silencing two asparagine synthetase genes using a technique called RNA interference.

Here is a cool video describing the process of RNA interference

Being able to specifically enhance or silence certain genes within the cells of the plant has also enabled researchers to control the potato’s ability to resist black spot bruise, something that can sig- nificantly affect productivity and amount of sellable product to market.

According to Simplot, up to 28% of potatoes like this in the United States are thrown away.

 image from https://www.agric.wa.gov.au/potatoes/improve-potato-quality-minimising-mechanical-damage

Black spot bruising occurs during transportation of potatoes where bumping can cause damage to cells underneath the skin. Often the way to see this is by cutting open the tuber.

The chemical question a curious student may ask is how asparagine changes to acrylamide. A detailed mechanism can be an interesting exercise for an organic chemistry student. Here is one proposal:

For more information:

*Ask the Regulators: Acrylamide, Furan, and the FDA
*Low-acrylamide French fries and potato chips, by C.M. Rommens, H. Yan, K. Swords, C. Richael, and J. Ye
*Innate technology by Simplot
*Acrylamide is formed in the Maillard reaction, by D.S. Mottram, B.L. Wedzicha, and A.T. Dodson