University of Prince Edward Island Lecture 7 Supplement: –

1 H Materials For Making Money Polysaccharides are produced by living things and can be extracted, processed Biochemistry6 7 8 CNO Barry Linkletter and modified to create valuable materials. We can make cheaper for your 15 16 SP soda pop and additives for thickening foods and consumer products. We can also make fibers for textiles and explosives for soldiers. Along the way we will make lots and lots of money. The biochemistry of polysaccharides is very important to industry. Biochemists are not all working in human health, many work in fields that use biomaterials for consumer products. So biochemistry is a great way to feed yourself (did you see Beer Uses what I just did there?). Malted barley is barley that has been allowed to germinate, then dried. The germination KeynoteChemistry.com activates that break down the starch in the barley seed to simpler sugars like - The video is available on YouTube at ose that yeast can metabolize to make delicious beer. https://youtu.be/tdSB0Y1UZYY The malting process causes the dormant seed to “awaken” and begin producing the enzymes that break down starch. The process is halted by drying and the starch and enzymes await rehydration and heating when you make the wort. Careful control of temperature and time will ensure the correct mix of sugars before you cool the wort and add the yeast. Understanding the biochemistry that occurs in barley grains as they germinate and as the wort is cooked is essential to The Bavarian beer purity law of 1516 states that beer may making a great beer. only contain barley, hops and water. Why did they not A tetrasaccharide is include adding yeast? bound in the active site of this amylase The Germans take this . seriously and so should you. No more blueberry ale. Amylase is a diastase, a class of starch digesting enzymes. Diastases were the first enzymes every isolated. Can you guess why?

Starch is not sweet. is much sweeter. Try tasting your wort α-Amylase is the enzyme that as the cooking procedure cleaves starch polymers and gives moves along. and trisaccharides like mannose as a product.

Introduction To Biochemistry: Polysaccharides: Commercial Applications 1 of 12 Most of the good-looking images of proteins in this presentation are stolen from David Goodsell’s King Corn “Molecule of the Month” at Corn is a major commodity crop. From the https://pdb101.rcsb.org/motm ancient Inca to the modern factory farm, corn has been a staple crop of the Americas and the world. From corn we can extract corn oil and cornstarch. Then we can use the rich Amylases Glucoamylase isomerase husks for ethanol production. We can feed cows with it and cows feed people. And many varieties of corn are also popular for human consumption. Cornstarch is cheap. The in cornstarch consist of polymers of glucose and can be Starch is hydrolyzed to glucose units. And then enabled to hydrolyzed by enzymes to give glucose . reach it’s equilibrium between and High Fructose Corn glucose. Cornstarch could be digested by acid to give high fructose but using enzymes will enable the process to occur under milder conditions. The reaction is very, very, very slow at neutral pH but enzymes are catalysts and accelerate the reaction. Step 1: Amylases are isolated by biotech companies and sold to industry. There are many sources and types of amylases. You will choose the supplier that suits your needs. Money changes hands. Step 2: We add amylases enymes to corn starch. With careful control of temperature and pH we will get maltose and other short chains of glucose as a product. Step 3: Maltose is not sweet enough for our needs so we use the enzyme glucoamylase to complete the digestions and hydrolyze the short oligosaccharides to glucose. Step 4: Pure tastes awful. To increase the of our glucose syrup we can convert some of it to fructose. The enzyme glucose isomerase can be used. At equilibrium the mixture will be just under 50% fructose. Fructose is much sweeter than glucose. You can easily arrange to have a syrup that is 42% fructose and 58% glucose. That exact mixture has the same sweetness as but is less expensive. Step 5: Replace cane sugar in your food manufacturing process with high fructose corn syrup. Put it in everything. Con- sumers just want the cheapest products, don’t they? It tastes almost the same. Then invest in plus-size clothing companies. Make money both ways.

“Alpha-amylase”, David Goodsell, Molecule of the Month, 2006, http://dx.doi.org/10.2210/rcsb_pdb/mom_2006_2 Introduction To Biochemistry: Polysaccharides: Commercial Applications Page 2 of 12 can Liquid Invert Sugar survive high Another common sweetener in processed food is liquid invert sugar. You temperatures. make this at home when you are cooking jam or making certain . Observe all the rigid β-sheet structures in Sucrose has a positive and so does glucose. Fructose has a this enzyme. They larger negative value for its optical rotation. So if you hydrolyze sucrose to are just like the a 50/50 mixture of fructose and glucose you will have a net negative optical crystaline regions of rotation. cellulose. They provide order and strength. Inverting sugar means to perform a reaction that results in the optical rota- tion reversing in value. This is a result of the of sucrose. This can be done in mild acid (fruit juices or a touch of lemon juice) and high tem- peratures (Boil that jam! Freezer jam is lame.) by using the enzyme invertase. HO Inverted sugar syrup is sweeter than sucrose and does not crystalize so OH HO OH candies can be made smooth and creamy, like cara- O O OH H2O O O mels. You can even pull stunts like mixing fondant HO OH HO (mostly sucrose) with invertase and then wrap it in HO O O OH HO OH H chocolate. Over time the crystaline sucrose will be OH HO OH converted to liquid invert sugar and nobody will OH HO 20 20 20 know how you got that sweet creamy filling inside [] = +66.4 [] = +52.7 [] = 92 the chocolate. But biochemists will know. D D D 20 The observed optical = 19.7 rotation is the average []D value of the mixture. is mostly Cornelius O’Sullivan (1841-1907) and Frederick William Thompson were HO invert sugar. Thanks pioneers in enzyme chemistry in the service of the brewing industry. they O OH bees, I’ll take that now. studied invertase and were the first to propose that enzymes form some HO OH sort of a complex with their substrates in 1890. This work led directly to Emil Fischer’s famous “lock & key” hypothesis.

HO HO HO HO HO OH OH O O O O O As we will soon see, invertase was the enzyme used by Michaelis and O O H O –H OH +H OH OH 2 OH OH HO HO Menten when they developed their famous equation for enzyme kinetics. HO O HO O HO HO OH2 HO OH OH H OH OH OH OH OH HO OH HO

OH Can you interpretGlucose 16 O the reaction mechanism HO O for acid catalyzed 32 H OH Hey, look! New technology HO hydrolysis of an acetal? Maltose 33 for making HFCS is being Fructose Now is a good time to developed all the time. Got review your organic Glucose 74 any ideas? chemistry. Honey 97 “Kinetics of Glucose Isomerization to Fructose by Immobilized Glucose Isomerase (Sweetzyme IT)”, A.M. Dehkordi, M.S. Tehrany, I. Safari, Ind. Eng. Chem. Res., 2009, 48, 3271–3278 .http://dx.doi.org/10.1021/ie800400b HFCS-42% 100 Introduction To Biochemistry: Polysaccharides: Commercial Applications Sucrose 100

Page 3 of 12 Fructose 173 It’s not all bad. was used for movie film and is still used as a Improving on Nature (Sort Of...) liquid bandage for cuts and scrapes. Cotton was king, then came the Civil War. The guns of the North and South used old fashioned dirty gunpowder that gummed up the grooves of the rifles and built up in the barrels of cannons. Gun barrels had to be cleaned constantly and sustained rapid fire was not possible. Enter cellulose. Cellulose was identified in 1838. And what do you do with something when you get your hands on it back then? You cook it in every acid that you can find. After processing in a mixture of nitric and sulfuric acid, cotton can be converted to “gun cotton”. It burns with no smoke or debris and was the first “smokless gunpowder”. In 1887 Alfred Nobel mixed it with nitroglycerin to make the first version of cordite. Improved mixtures of cordite propelled the world’s bullets from the Boer War to the present. Where do you think all that money comes from for those fancy science medals?

All the oxygen needed Gunpowder is essentially a mixture of carbon black and to burn is now part of potassium nitrate. Compare it to nitrocellulose. the molecule. O O O O O O O O O O O O O O O O N O N O N O N O N O N O N O N O N O N O N O N O N O N O N O O O O O O O O O O O O O O O O O O O O O O O O O O O O O O O O O O O O O O O O O O O O O O O N O O N O O N O O N O O N O N O N O N O N O N O O N O O N O O N O O N O O O O O O O O O O In 1845, Schönbein developed the first Charges are Nobel took the work of Sobrero practical synthesis of gun cotton. He not shown for and used nitroglycerin as a key also invented the fuel cell.. simplicity. component in his inventions of dynamite, gelignite and ballistite (cordite). Nobel’s brother died working with nitroglycerin at their dad’s munitions factory. Nobel saw the Alfred Nobel need for a more stable Emil Nobel explosive. Three years 1843-1864 1833-1896 later he had dynamite. Sobrero created nitroglycerin. He was terrified of it. He alternated Gelignite was also a criticizing Nobel for commercializing mixture of nitrocellulose Christian Friedrich Schönbein Ascanio Sobrero an agent of death & destruction with and nitroglycerin. Ironic fact: Near the end 1799-1868 1812-1888 demands for credit and recognition of his life, Nobel was of his invention. prescribed nitroglycerin for his heart condition.

Cordite in a rifle round.

Introduction To Biochemistry: Polysaccharides: Commercial Applications Page 4 of 12 The & Paper Research Instutute Biochemistry And Wealth at McGill University Cellulose may look simple, but its processing and preparation are multi-billion dollar industries. Where does your cellulose come from – wood, cotton, hemp, jute, linen or some other source? Textiles, ropes, paper and many other products are is an assortment dependant on the extraction and processing of cellulose. of crosslinked polyphenolic subunits. It’s what gums up Pulp and paper chemistry is an economically important field of your sandpaper if you study. Much effort has gone into understanding the biochemis- press too hard. try of cellulose and lignin in an effort to develop less obnoxious pulping methods. Lignin is a biopolymer of phenolic and other compounds. It is perhaps the closest thing to plastic that nature makes. It provides strength to plant cell walls by combining with the cellu- lose to make a composite material. Just like carbon fiber and , cellulose fiber and lignin can make an incredibly strong material. Lignin is why trees can grow so big. Finding better ways to remove lignin to extract cellulose from wood pulp is what makes some chemists so rich. McGill has a building dedicated to Pulp and paper research. They Keller and Fenerty once had a “Department of independantly developed Cellulose Chemistry”. the first method for pulping wood in 1844. You can see the Scott as you approach the Caribou Ferry Fenerty was a Canadian terminal. You sometimes can smell it from Sackville, N.S. from Wood Islands. His legacy lives on in Pictou, N.S.

Friedrich Keller Charles Fenerty 1816-1895 1821-1892 Cotton is a good source of cellulose for paper but trees are HUGE. If only we could extract cellulose from wood. We can — for an evironmental price.

Introduction To Biochemistry: Polysaccharides: Commercial Applications Page 5 of 12 Crystalline region of Amorphous Making Money From Goo cellulose fiber A valuable form of cellulose is microcrystaline cellulose. Native cellulose consists of crystaline and amorphous domains. the amorphous domains are more accessible to solvent and acid hydrolysis of these portions of the poly- mer is faster than in the more organized crystaline domains. With care we can convert polymeric cellulose to a material composed of the crystaline H SO domains. This material has found uses as an binder in drug formulations and 2 4 in pill coatings. Microcrystaline If you have ever enjoyed tasty mussels at a fine restaurant you have likely cellulose eaten Prince Edward Island mussels. In recent years the mussel industry has been challenged by invasive species of tunicates. These sea squirts are invertibrate filter feeders and attach to a grow on the mussels. They are mostly wtare and add enormous weight to the mussell socks. this damages equipmemnt and slows harvesting. They also compete for the same food as mussels. Mussel growers must remove the tunicates from the mussel socks. Inventer a better tunicate shredder and make money. Researchers have learned that How can MICROcrystaline tunicates are rich in cellulose and that tunicate cellulose is much more crys- cellulose make NANOwhiskers? taline than plant cellulose. Microcrystaline cellulose sourced from annoying It’s like imagining a mouse invasive tunicates has longer fibres than other forms. It is suitable for eating an elephant. I propose strengthening nanocomposite materials. It could be marketed as a “green” a U.N. commission that regulates form of carbon fibre. Perhaps you will be the one to develop a better way the use of the word “nano”. to extract or process tunicate cellulose. Money! Cellulose nanowhiskers are ten times longer when microcrystaline cellulose from tunicates is used.

I smell money!

“Nano, nano.”

Extract the cellulose Profit ! Without predators, invasive Knock them off and develop a proprietary tunicates cover everything and dry them process for making the around. out. Sell them for microcrystaline version. their special cellulose.

Introduction To Biochemistry: Polysaccharides: Commercial Applications Page 6 of 12 Galactose is an epimer of glucose at the 4- Lobster Jam position. There are many other polysaccharides that provide structure and Pectin is a polymer of several sugars. A common form function in biochemistry. Many are polymers of modified sugars is a homopolymer of galacturonic acid (oxidized galac- – either oxidized, aminated or combined with other metabolites tose) connected by α(1→4) linkages. like pyruvate. an α —1 →4 link

CH3 CH 3 CH3 CH3 CH3 O O O O O O O O O O O O O O O O O O O O O O O O O O O O O O O O O O O O O O OH O O O O O O O O O OH OH OH OH OH OH OH OH OH OH HO HO HO HO HO HO HO HO HO HO HO HO Observe that many of the OH acid groups are methylated. O HO When these methyl esters are O O HO hydrolyzed, methanol is produced. O HO O This can happen during OH OH HO OH of alcohol so some drinks might have O O Henri Braconnot O HO OH 1780-1855 a slight bit of extra “kick” depending O on the source of the malt. HO OH →4 link Braconnot discovered Compare an α —1 O in 1811 and pectin in 1825. He between with α —1 →4 link between . also demonstrated that sugar an See what a difference a single could be obtained from the acid change in a stereocentre can make? digestion of cellulose. Along the way he created an early form of Chitin β → nitrocellulose. is a polymer of (1 4) linked N-acetylglucosamine. Compare the backbone to cellulose. Chitin is used as a structural in arthropods. Lobster shells are rich in chitin.

CH3 CH3 CH3 CH3 CH3 O O O O O HO NH HO O NH HO O NH HO O NH HO O NH O HO HO HO HO HO O O O O O O O O O O HO HO HO HO HO NH HO O NH HO O NH HO O NH HO O NH HO O O O O O O Hofmann solved the CH3 CH3 CH3 CH3 CH3 structure of chitin in 1928. He went on to If you hydrolyze the amide make another famous groups with hydroxide you molecule. Can you guess will get chitosan. HO O what it is? O O Albert Hofmann HO 1906-2008 NH2

Introduction To Biochemistry: Polysaccharides: Commercial Applications Page 7 of 10 Walther Hess was the first The Gel of Biochemistry to use agar as a support Pectin and gelatin will make a nice gel for you but that gel will for growing bacteria. melt at low temperatures. Chefs have known for a very long Legend says that Hess noticed that time that if you want to make a gel pastry that won’t melt you his wife, Angelina Fannie, had prepared must use agar. Biochemists and microbiologists then “discov- gelatin deserts that didn’t melt on a ered” it in the 1880s. The major component of agar is agarose. hot day in the Alps. She had used agar.

Agarose is a slightly more complicated polymer but is is based on galactose units connected by β(1→4) and α(1→3) linkages. Angelina Fannie Walther Hesse 1846-1911 α —1 →3 link 4 link an β —1 → a OH HO OH HO OH HO OH HO OH HO OH O HO O HO O HO O HO O HO HO O O O O O O O O O O O O O O O O O OH OH OH OH OH OH O O O O O O The two sugars are That’s right! An L-sugar. β OH HO -D-galactose and Can you see the “L” in HO α-L-3,6-anhydrogalactose. the second galactose unit? O O OH Notice how the 6’carbon OH HO (in the cycliccyc li c ether)ether) isis HO down rather than up? OH OH OH β-D-galactose α-L-galactose

Agar was discovered in 1658 by a japanese innkeeper, Mino Tarōzaemon. It is made up of the biopolymer agarose. Without agar we It forms gels that are stable at 37˚ and wouldn’t have these thus is a good support for growing yummy treats. bacteria.

Now anyone can grow gross things in Petri Gelidium Almansi is a red algae that is dishes; thanks to agar. an important commercial source of agar. Julius Richard Petri 1852-1921 We will explore agarose gel electrophoresis later Introduction To Biochemistry: Polysaccharides: Commercial Applications in this course. Page 8 of 12 The Gel of the Food Industry Carrageenan is a similar to agarose. Except the anhydrogalac- There are several common polysccharide gelling agents used in tose units are derived from D-galactose, not L. The repeating the processed food industry. A familiar one is carragennan. galactose units are connected by β(1→4) and α(1→3) linkages. Compare it to agarose.

4 link β —1 → a O O O O O O O O O O O S S S S S H O OH O O OH O O OH O O OH O O OH O O OH O O O O O O O O O O O O O O O O O O O O O O O O O O O O OH OH OH OH OH OH HO HO HO HO HO Carrageenan has sulfate groups an α —1 →3 link that give it an ionic character HO OH OH and a negative charge. HO Flip the ring OH HO O O OH O HO OH HO HO OH OH Carrageenan is used for OH OH many reasons in food. It -D -D gives soy and almond milk α -galactose β -galactose drinks a thicker “mouth Irish Moss gatherers collect it in the feel”. Chondrus Crispus is a red algae that is a major shallows after a storm by using horse- source of carrageenan. It is known as “Irish drawn baskets. It is cleaned, dried Moss” on the atlantic coast of North America and sold to processors.

Introduction To Biochemistry: Polysaccharides: Commercial Applications Page 9 of 12 There is an error Many sugars look complex but in the structure of All Those Gums are just combinations of simpler xanthan gum presented Xanthan Gum molecules on this page. Can What is ? It is another common thickener in you spot it? foods and shampoos. It is a polysaccharide produced by a lactic acid bacteria. It was commercialized in the 1960s and you now O O O O find it everywhere. The main chain is a H C O HO HO O HO β —1 →4 linked polymer 3 H3C of glucose, just like cellulose. HO O O O HO OH HO OH On every second glucose (on average) is a trisaccharide with anionic groups.

O O O O O O O O O O H3C H3C Mannose H3C H3C condensed with O O O O O O O pyruvate O O HO HO HO HO HO HO HO HO HO HO O O O O O

O O O O β —1→4 O O O O O O HO O HO O HO O Glucuronic HO O HO O acid

O O O O O O O O O O HO HO HO HO HO H3C HO H3C HO H3C HO β —1→2 H3C HO H3C HO O O O O Mannose O O O O O O HO HO condensed with HO HO HO O O acetic acid O O O α —1→3 HO OH HO O OH HO O OH HO O OH HO O OH O O O O O O O O O O O O O O O O O HO HO HO HO HO OH HO O OH HO O OH HO O OH HO O OH HO O

All those gums that you see in ingredient lists are polysaccha- rides derived from bacteria or plants. I am sure that some- Allene Jeans developed where, someone is finding a new source of gum and hoping to a method for mass producing commercialize it for food thickening and money making. dextran in the 1950s. She also invented a method for producing Look for Guar Gum, Locust Bean Gum, Gellan Gum and many Allene Jeans xanthan gum, another polysaccharide others as you tour your local grocery store. 1906-1995 that is used as a gelling agent.

Introduction To Biochemistry: Polysaccharides: Commercial Applications Page 10 of 12 This Is Only The Very Beginning... This presentation was never intended to provide all the information that you are required to digest for this course of study. By definition, univer- sity requires that you read books, think about what you have read, and ask questions. Otherwise stay at home, watch TV and save your money. Always consider the relatively brief presentation in class to be a mere apéritif for your studies. I cannot read the textbook to you but I do hope to highlight some important topics, provide stories and context to pique your interest in biochemistry and to inform you of current research challenges to which you might someday make a contribution. As you read your textbook and consider this presentation, strive to master the following essential skills of biochemistry.

Topics Highlighted in this Brief Presentation This presentation was mostly to acquaint you with the commercial world of biochemistry and the value of biomaterials in general. Processing of these materials into commodities like xantan gum and high fructose involves the use of enzymes. Biochemistry is very important to the commercial food industry. Can you calculate the expected optical rotation of a given mixture of glucose and fructose? What is the role of amylase in the digestion of food?

This gelled sangria is a concoction from the molecular gastronomy movement. I’m not a fan of this hipster stuff but at least it uses xanthan The video is available on YouTube at https://youtu.be/tdSB0Y1UZYY gum in the recipe. Would you serve this as an aperitif? Do you drink it or eat it with a spoon?

KeynoteChemistry.com

Introduction To Biochemistry: Polysaccharides: Commercial Applications Page 11 of 12 References and Notes I have used many images to decorate this presentation. Some of them are in the public domain and some are not. I claim fair use for educational purposes.

Images of amylase, glucomylase and glucose isomerase from “Alpha-amylase”, David Goodsell, Molecule of the Month, 2006, http://dx.doi.org/10.2210/rcsb_pdb/mom_2006_2

Images of Bavarian Beer Law, barley & malt, corn cob and poster of corn products accessed on July 25, 2015 at https://beerography.wordpress.com/2013/07/10/reinheitgebot-the-bavarian-beer-purity-law-explained/ http://hdwallpick.com/free-barley-background.html http://www.wpclipart.com/food/vegetables/corn/corn_on_the_cob_large.jpg.html https://en.wikipedia.org/wiki/Corn_starch

Images of Cadbury Cream Egg and honeycomb with bees accessed on July 25, 2015 at http://www.powerfmbegabay.com.au/the-big-breakky/47389-how-can-you-make-a-cadbury-creme-egg-better http://genius.com/4810237

Images of Christian Friedrich Schönbein, Ascanio Sobrero, Alfred Nobel and Emil Nobel accessed on July 15, 2015 at https://commons.wikimedia.org/wiki/File:Christian_Friedrich_Schönbein_Litho.jpg https://en.wikipedia.org/wiki/Ascanio_Sobrero http://www.livescience.com/48157-nobel-prize-medicine-for-brain-gps.html https://upload.wikimedia.org/wikipedia/commons/1/10/Emil_Nobel.jpg

“Charging On Foot With The Lance: Bengal Lancers Attack German Trenches, October 24, At Ramscapelle, Near The Yser”, From the Painting by R. Caton Woodville accessed on July 15, 2015 at http://www.gutenberg.org/files/18333/18333-h/18333-h.htm

Images of McGill PPRI, Lignin structure, Friedrich Gottlob Keller & Charles Fenerty http://cac.mcgill.ca/campus/buildings/Pulp_Paper_Research_Institute.html https://commons.wikimedia.org/wiki/File:Lignin_structure.svg https://en.wikipedia.org/wiki/Friedrich_Gottlob_Keller http://www.charlesfenerty.ca

Images of cotton, editorial cartoon, Scott & birch tree trunk accessed on July 15, 2015 at http://homeguides.sfgate.com/cotton-biodegradable-78494.html Image of stamp accessed on December 1, 2016 at http://thechronicleherald.ca/sites/default/files/u23/deAdder1.jpg https://en.wikipedia.org/wiki/Reinheitsgebot http://thechronicleherald.ca/editorials/1226879-editorial-nova-scotia-should-charge-polluting-northern-pulp-mill http://www.dreamstime.com/stock-images-birch-tree-trunk-image28505534

Images of Pliny the Elder and page from “Natural History” accessed on July 15, 2015 http://www.crystalinks.com/pliny.html Image of Mork from Ork accessed on December 1, 2016 at https://www.pinterest.com/sharikohut/robin-williams/ http://sites.davidson.edu/aroundthed/early-histories-2/

Images of Henri Braconnet, cert box, Kerr jam jar & chitosan bottle accessed on July 15, 2015 at “Le pharmacien et chimiste Henri Braconnot (Commercy 1780-Nancy 1855)”, Becq, C.; Labrude, P.; Revue d'histoire de la pharmacie, 2003, 91, 61-78, http://dx.doi.org/10.3406/pharm.2003.5479 http://www.kraftcanada.com/brands/certo Image of tunicates in water accessed on December 1, 2016 at http://annstreetstudio.com/tag/mason-jar/ https://www.princeedwardisland.ca/en/information/agriculture-and-fisheries/aquatic-invasive-species http://www.onlynaturalinc.com/products/tablets/chitosan-fat-blocker-172 Image of dried tunicates in water accessed on December 1, 2016 at http://www.exoticsguide.org/styela_clava Image of cellulose nanowhiskers from “Transmission Electron Microscopy for the Characterization of Cellulose Nanocrystals”, Images of Albert Hofmann, Sandoz LSD bottle and lobster accessed on July 15, 2015 at Madhu Kaushik, et. al., in "The Transmission Electron Microscope - Theory and Applications", 2015, Khan Maaz (Ed.), http://likesuccess.com/author/albert-hofmann INTECH, pp 129-163, http://dx.doi.org/10.5772/59457 http://www.blotterbanks.de/images/product_images/original_images/216_0.jpg http://sushiyamaonline.com/menuitems/florida-lobster/

Images of Angelina Fannie and Walther Hesse, Gelidium Almansi red algae, agar petri dish, gel desert, Julius Petri & agarose electrophoresis gel accessed on July 15, 2015 at http://voer.edu.vn/m/moi-truong-nuoi-cay-culture-medium/e29607b0 http://www.naris.go.kr/v2/naris_search/search_result_detail.jsp?inst_id=1314761 http://www.wisegeek.com/what-is-agar.htm# http://i.ytimg.com/vi/YmdwM4fWezc/maxresdefault.jpg http://www.tagseoblog.com/bacterial-doodle-for-julius-richard-petri https://commons.wikimedia.org/wiki/File:Agarose_gel_slab_for_DNA_Analysis,_after_the_Electrophoresis_run.jpg

Images of Nutritional information label, soy milk drink box, Irish Moss, moss gathering at the show and Allene Jeans accessed on July 15, 2015 at http://www.8thcontinent.com/site-media/images/products/vanilla.gif https://silk.com/products/original-soymilk https://en.wikipedia.org/wiki/Chondrus_crispus http://www.fao.org/docrep/x5819e/x5819e05.jpg http://www.chemheritage.org/discover/online-resources/chemistry-in-history/themes/public-and-environmental-health/food-chemistry-and-nutrition/jeanes.aspx http://www.molecularrecipes.com/molecular-mixology/white-sangria-suspension/ Errors and Worse This presentation contains mistakes, typographical errors, crimes of grammar and worse. All mistakes are intentional – to see if you are paying attention. Report any errors that you find in the class forum. The first to spot and report an error will win a fabulous invisible prize. Introduction To Biochemistry: Polysaccharides: Commercial Applications Page 12 of 12