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CHM 1040 – General, Organic, and Biochemistry for Health Sciences

CHM 1040 – General, Organic, and Biochemistry for Health Sciences. Office Hours W: 3:30 – 4:30 TR: 1:00 – 2:00 MF: 10:30 – 11:30 Usually available MWF 9:30 – 2:00 TR AM. Dr. Paul Stein Office: S3305 Lab: S3313A pstein@css.edu Phone - 6065.

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CHM 1040 – General, Organic, and Biochemistry for Health Sciences

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  1. CHM 1040 – General, Organic, and Biochemistry for Health Sciences Office Hours W: 3:30 – 4:30 TR: 1:00 – 2:00 MF: 10:30 – 11:30 Usually available MWF 9:30 – 2:00 TR AM Dr. Paul Stein Office: S3305 Lab: S3313A pstein@css.edu Phone - 6065 SI sessions (Supplemental Instruction) Nicole Jackson - SI Leader Times: Tuesday 4:00 – 6:00 - S2139 Thursday 6:00-8:00 S2203

  2. 5- Carbohydrates (Chapter 6 in newer version of text) Classes of Carbohydrates Functional Groups in Monosaccharides Stereochemistry in Monosaccharides Reactions of Monosaccharides Disaccharides Polysaccharides Carbohydrates and Blood

  3. 5- Carbohydrates • Functional Groups in Monosaccharides Carbohydrates are polyhydroxyaldehydes or ketones and their derivatives. They are named by the general formula – Cn(H2O)n. However, the classification has broadened so that not all carbohydrates have this general formula. The simplest carbohydrate is glyceraldehye, C3H6O3. H C = O | H – C – OH | CH2 - OH C2 is chiral so there are D and L forms The optical isomer shown is D

  4. Carbohydrate = Saccharide • Sugars = mono, or disaccharides • Classes of Carbohydrates • # of carbons – • Glyceraldyde is a triose. • Pentoses (ribose), and hexoses (glucose and fructose), and most key biological • monosaccharides have 5 or 6 carbons. • # of monosaccharide (hexose) units– • monosaccharide – one hexose units. • disaccharides, tri-, tetra- , etc. (also called oligosaccharides) • Sucrose (table sugar), lactose, and maltose are disaccharides. • polysaccharides – polymers with many saccharide units linked together. • Starch (amylose & amylopectin), glycogen, and cellulose are all polysaccharides • made from glucose.

  5. Glucose (aldose) and Fructose (ketose) have the general formula C6H12O6. They are hexoses (6 carbons) • Stereochemistry in Monosaccharides Fructose and Glucose are …. a) structural isomers b) cis-trans isomers c) optical or stereoisomers * * * How many chiral carbons are present in glucose? a) 1 b) 2 c) 4 d) 6 * The highest numbered chitral C determines D (right) vs. L (Left). D-Fructose D-Glucose

  6. Stereochemistry in Monosaccharides L – glucose is the complete mirror image of D - glucose. Naturally occurring carbohydrates contain only D – sugars.

  7. Aldehydes and Alcohols react to form a new functional group … Hemiacetal H H R – C + HO - R' → R – C – O - R' || | O OH

  8. Glucose has a ring structure a – D - glucose anomers b – D - glucose Monosaccharides contain both a carbonyl and several hydroxyl (alcohol) functional groups. They form internal hemiacetals making a ring structure. There are two possible ways the ring can close. Both of these forms exist in sugar solutions. There is << 1% of the “open” or aldehyde form remaining.

  9. Reactions of Monosaccharides Glucose forms a 6-membered ring structure a – D - glucose anomers b – D - glucose

  10. 5- Carbohydrates Functional Groups in Monosaccharides Carbohydrates are polyhydroxyaldehydes or ketones and their derivatives. Carbohydrates typically have one or more chiral carbons. Thus many carbohydrates have multiple optical isomers. Glucose (with 4 chiral carbons) is part of a family of 16 optical isomers. Aldehydes and Alcohols react to form a new functional group … Hemiacetal H H R – C + HO - R' → R – C – O - R' || | O OH

  11. Glucose (an aldohexose), and fructose (a ketohexose) are two common sugars. They are structural isomers with the identical formula of C6H12O6. * * * * D-Fructose D-Glucose

  12. Stereochemistry in Monosaccharides L – glucose is the complete mirror image of D - glucose. Naturally occurring carbohydrates contain only D – sugars. D - Galactose is one of many optical isomers of glucose that are not mirror images. Draw the cyclic form of … D-glucose D-galactose

  13. Reactions of Monosaccharides Glucose forms a 6-membered ring structure % in solution ~ 36% Hemiacetal anomeric C1 % in solution << 1% a – D - glucose anomers b – D - glucose % in solution ~ 64%

  14. Benedict’s Test for “reducing sugars” Aldehydes (and some ketones) can be oxidized to form carboxylic acids. Benedict’s solution contains Cu2+ ions and is blue. It reacts with sugars that have an open or aldehyde/ketone form. The sugar gets oxidized to a carboxylic acid The Cu2+ ions get reduced to Cu1+ ions which then form a red ppt – Cu2O. Name Cu2O. If a cyclic sugar structure has a hemiacetal functional group …. then it will react with Benedict’s solution to form a red ppt. This is because all cyclic sugars with hemiacetals can open and then react with Cu2+.

  15. Benedict’s Test for “reducing sugars” At one time this was used as a urine test to indicate diabetes. It has long been replaced with more accurate and sensitive tests using enzymes. If a cyclic sugar structure has a hemiacetal functional group …. then it will react with Benedict’s solution to form a red ppt. This is because all cyclic sugars with hemiacetals can open and then react with Cu2+.

  16. Reactions of Monosaccharides Fructose forms a 5 – membered ring Is fructose a reducing sugar? (or will it react with Benedict’s solution?) a) yes b) no a – D - fructcose anomers b – D - fructose

  17. Found in …. DNA Deoxyribonucleic acid Found in … RNA Ribonucleic acid Riboflavin vitamin

  18. Isomer terminology in Sugars Structural isomers a – D - fructose Enantiomers Optical isomer that are mirror images Diasteromers Optical isomer but not mirror image a – D - glucose anomers D-Glucose b – D - glucose

  19. Linking monosaccharides together → + + H2O Acetal bond or glycosidic bond a1-4 Hemiacetal anomeric C acetal anomeric C Hemiacetal anomeric C Maltose Is maltose a reducing sugar? (or will it react with Benedict’s solution?) a) yes b) no

  20. Figure 6.12 Three Important Disaccharides—Maltose • Maltose, or malt sugar, is a disaccharide formed in the breakdown of starch. • Malted barley contains high levels of maltose. The glucose in the maltose of malted barley can be converted to alcohol by yeast. • The glycosidic bond in maltose is a(1→4). • Maltose is a reducing sugar.

  21. 6.5 Disaccharides glycosidic bond b1-4 Three Important Disaccharides—Lactose • Lactose, or milk sugar, is found in mammalian milk. • Intolerance to lactose occurs in people without lactase. • When lactose remains undigested, intestinal bacteria break it down, producing abdominal gas and cramping. • The glycosidic bond in lactose is b(1→4): it occurs between C1 of a b-galactose and C4 of a glucose. • Because the anomeric carbon on the glucose unit is free (not in a glycosidic bond), lactose is a reducing sugar. Figure 6.13

  22. 6.5 Disaccharides acetal anomeric C1 acetal anomeric C2 Three Important Disaccharides—Sucrose • Sucrose is the most abundant disaccharide in nature: sucrose is found in sugar cane and sugar beets. • When glucose and fructose join in an a,b(1→2) glycosidic bond, sucrose is formed. • Both anomeric carbons are bonded (carbon 1 of glucose and carbon 2 of fructose). Because there is no free anomeric carbon, sucrose is not a reducing sugar. a1-b2 Glycosidic bond Figure 6.14

  23. Exam Make-up 20 multiple choice (2 pts each) hydrocarbons – alkanes, alkenes, alkynes recognizing functional groups – alcohols, carboxylic acids, amines, esters, amides, hemiacetals, acetals carbohydrate concepts isomers and isomer types fatty acids aromatic hydrocarbons blood type concepts 5 written answer questions (60 pts) 25 Drawing organic structures from names – condensed structural formulas, Lewis structures, skeletal structures 10 Giving names for structures 10 isomer concepts applied to hydrocarbon structures 15 carbohydrate structures – open and cyclic forms, a/banomers, glycosidic bonds

  24. This compound is …… a) sucrose b) maltose c) lactose d) fructose e) a nonreducing sugar 2. The glycosidic bond in maltose is …… a) a1-4 b) b1-4 c) a1-6 d) a1-a4 Name the functional group represented by the C matching the correct # …….. a) hemiacetal b) aldehyde c) acetal d) alcohol e) ether 6 3 5 4

  25. # of monosaccharide (hexose) units– monosaccharide – one hexose units. disaccharides, tri-, tetra- , etc. (also called oligosaccharides) Sucrose (table sugar), lactose, and maltose are disaccharides. polysaccharides – polymers with many saccharide units linked together. Starch (amylose & amylopectin), glycogen, and cellulose are all polysaccharides made from glucose. Polysaccharides from glucose ….. Starch(plant cells) function – glucose storage amylose: a1-4 amylopectin: a1-4 and a1-6 (~every 12 units) Cellulose: (plant cells) function – plant cell wall structure b1-4 Glycogen (animal cells – liver/muscle) function – glucose storage a1-4 and a1-6 (~every 7 units)

  26. Polysaccharides from glucose ….. Starch(plant cells) function – glucose storage amylose: a1-4 amylopectin: a1-4 and a1-6 (~every 12 units) Cellulose: (plant cells) function – plant cell wall structure b1-4 Glycogen (animal cells – liver/muscle) function – glucose storage a1-4 and a1-6 (~every 7 units)

  27. Exists in plant cells as small granules Small insoluble particles Hydrated (surrounded by water) Starch(plant cells) function – glucose storage amylose: a1-4 amylopectin: a1-4 and a1-6 (~every 12 units)

  28. amylose amylopectin: a1-4 and a1-6 Hydrolysis (same as digestion) Break glycosidic bonds (lysis) by adding water (hydro) in cells or intestines this is done by enzymes (amylase + maltase) in lab you did this by adding acid Complete hydrolysis produces many glucose units Starch + H2O → Glucose Maltose, or malt sugar, is a disaccharide formed in the breakdown of starch.

  29. Cellulose: b1-4 (plant cells) function – plant cell wall structure Structural Polysaccharides: Cellulose • Cellulose contains b(1→4)-bonded glucose units. • This change in bond configuration completely alters the overall structure of cellulose compared with that of amylose. • Whereas amylose coils, the b-bonded chain of cellulose is straight. • Many of these straight chains of cellulose align next to each other, forming a strong, rigid structure. • We cannot digest cellulose, but it is still an important part of our diet because it assists with digestive movement in the small and large intestine. This is the main component of dietary fiber.

  30. | NH | C = O | CH3 | NH | C = O | CH3 Structural Polysaccharides: Chitin • Chitin is made up of a modified b-D-glucose called N-acetylglucosamine with b(1→4) glycosidic bonds. • Like cellulose, chitin is a strong material with many uses, one of which is a surgical thread that biodegrades as a wound heals. • Chitin is present in many insects’ exoskeletons and serves to protect them from water. Because of this property, chitin can be used to waterproof paper. • When ground, chitin becomes a powder that holds in moisture, and it can be added to cosmetics and lotions. | NH | C = O | CH3

  31. Storage Polysaccharides: Glycogen • Glycogen is the storage polysaccharide found in animals. • Most glycogen stores are located in the liver and in muscles. • Glycogen is identical in structure to amylopectin except that a(1→6) branching occurs about every 12 glucose units. • Glycogen is in the liver to maintain constant glucose levels in the blood when sugars are not being consumed. • The large amount of branching in this molecule allows for quick hydrolysis when glucose is needed.

  32. a-1,4 a-1,6 OH OH O O OH OH O O OH OH OH OH OH O O O OH OH O O OH OH OH Glycogen (& amylopectin of starch) OH O OH etc.

  33. GLYCOGEN

  34. Fuc Gal GlcNAc Gal Ser Fuc Gal GlcNAc Gal Ser Fuc Gal GlcNAc Gal Ser GalNAc Gal Blood Types & GlycosylTransferases (EC 2.4) Early stop codon mutation in glycosyltransferase gene results in nonfunctional enzyme A vs. B glycosyltranferase enzymes differ in sequence in only 4/354 residues. H-antigen RBC glycoprotein A B O

  35. What is your blood Type? a) A b) B c) O d) AB e) don’t know What is your RH factor? a) + b) - c) don’t know

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