BIO 1: Intro, Carbohydrates

Scientific study of life at the molecular level.

Biochemistry

What are the biomolecules involved with metabolism (energy, metabolic pathway)?

Carbohydrates, lipids, and proteins

What biomolecule is involved in the central dogma (RNA DNA genetic product)?

Nucleic acids

What are the basic building blocks of living organisms, responsible for carrying out all functions essential for life?

Cells

Differentiate Prokaryotic vs Eukaryotic cells: in terms of presence of organelles, structure, and function.

Prokaryotic: no nucleus, smaller and simpler with less organelles (cell wall, plasma membrane, DNA in cytosol, ribosomes), present in bacteria and archaea.

Eukaryotic: with nucleus, larger and more complex organelles present, present in animals, plants, fungi, and protists.

4 Levels of Cell Organization

1. Monomeric Units (biomolecules)

2. Macromolecules (made of 1 type of biomolecule)

3. Supramolecules complexes (made of 2+ type of biomolecule)

4. Cell and organelles

____ are specialized structures within a cell that perform specific functions essential for the cell’s survival and activity.

Organelles

5 Major Organelles: Function, Presence in Prokaryote/Eukaryote

5 Less Major Organelles: Function, Presence in Prokaryote/Eukaryote

What organelle produces secretory vesicles?

Golgi apparatus

Why is vacuole larger in plants?

Plants use the vacuole as a rigid wall cell structure (when full with water will swell and push against cell wall “turgor pressure”). Plants are stationary, need more water reserves.

Differentiate smooth and rough ER.

Smooth ER synthesizes lipids and carbohydrates

Rough ER has ribosomes attached, aids in processing of protein synthesis

Both are used in “post modification” of biomolecules

What is cytosol?

Cytosol is the aqueous component of the cytoplasm, where cellular processes occur, and it contains various organelles, proteins, and other substances essential for cell function.

What 4 chemical characteristics make water essential for biological systems?

Water is the most abundant molecule in the human body, at ____%.

70%

Water: Adhesion vs Cohesion

Cohesion - attraction between H2O-H2O
Adhesion - attraction between H2O-surfaces

Water: Key Physical Properties

Which organelle is single, semi-double, or double membraned?

Lysosome - single membrane (need easy in out of digestive enzymes)

Rough ER - semi-double

Nucleus - double

Chloroplast - double

______ are polyhydroxy aldehydes and ketones, or compounds that can be hydrolyzed into them.

Carbohydrates

What configuration of carbohydrates are naturally occurring? D or L?

D

α vs β: which has a dynamic/functional role, and which has a structural role?

α = dynamic/functional role

β = structural role

General formula of carbs

Cn H2n On

What type of bond does carbohydrate have?

Glycosidic bond

Classifications of Carbohydrates

Simple or complex

Monosaccharide

Disaccharide

Monosaccharides: Classification based on Length of C, and Functional Group location

Length of C: Triose, Tetrose, Pentose, Hexose

Functional Group: Aldose C1 aldehyde, Ketose C2 ketone

Chirality vs Optical Rotation: D-L vs d-l

D and L - “absolute configuration,” D-right + L-left, most chiral furthest C from top

d and l - optical rotation d (+) and l (-), needs polarimeter

Name 15 most common monosaccharides.

GET Ribs Are Xtra Lean

All Altruists Gladly Make Gum In Gallon Tanks

1. Glyceraldehyde Erythrose Threose Ribose Arabinose Xylose Lyxose

2. Allose Altrose Glucose Mannose Gulose Idose Galactose Talose

_______ are diastereomers that differ in the configuration around one stereogenic center only. Give examples.

Epimers / Epimeric pairs 

Galactose-Glucose C4

Glucose-Mannose C2

What new stereogenic center is formed after the cyclization of monosaccharides?

Anomeric carbon. 

α baba (pababa) trans

β up (beh taas) cis

(β -D-glucose at equi is 67% more preferred to form)

When pure α + β glucose anomers are dissolved in water, their optical rotation gradually changes, a phenomenon known as _____, which occurs due to ring-chain tautomerism, α + β interconverts until equilibrium

Mutarotation

Monosaccharides Reactions: Hemiacetal and OH group

1. Glycoside formation | Anomeric C OH →  OR α + β (HCl) 

2. N-Glycoside formation | Anomeric C OH → NHR α + β (mild H)

3. Ether formation | all OH → OR (Ag2O RX)

4. Ester formation | all OH → OAc (Ac2O or AcCl, pyr)

1,2 mild formation

3,4 strong formation

Monosaccharides Reactions: Carboxyl group

1. Reduction of Aldose | CHO @C1 → CH2OH “alditol” (NaBH4 CH3OH)

2. Oxidation of Aldose | both ends → COOH 1 end OR 2 COOH both → aldonic-mild Ox OR aldaric -strong ox agent ([O]) (

3. Wohl degradation | -HCOH @C2  (NH2OH Ac2O,NaOAc NaOCH3)

4. Kiliani-Fischer synthesis | +HCOH @C2 → left OH + right OH (NaCN,HCl H2,Pd-BaSO4 H3O)

_____ is the covalent linkage between 2 monosaccharides, formed through dehydration reaction that eliminates water molecule.

Glycosidic bond (OH-OH at C1,4 or C1,6)

Reducing vs Nonreducing Sugar 

Reducing sugar = still has 1 free anomeric carbon (not linked)

Non-reducing sugar = 2 anomeric carbons are linked (e.g. sugar)

Simple vs Complex Carbohydrates

Simple Carbohydrates (mono) = can’t be hydrolyzed into smaller molecules

Complex Carbohydrates (oligo- poly-) =  made of 2 or more simple sugars 

Differentiate oligosaccharides, disaccharides, trisaccharides, and hetero/homo polysaccharides.

Oligo = 2-10 monosaccharides

Disaccharides = 2 monosaccharides

Trisaccharides = 3 monosaccharides

Polysaccharides = 2+ monosaccharides

Homopolysaccharides = one type of monosaccharides

Heteropolysaccharides = 2+ type of monosaccharides

Give 6 most common oligosaccharides + common name + composition

1. Sucrose = table sugar = gluc + fruc (α1, β2)

2. Maltose = malt sugar = gluc + gluc (α1,4)

3. Lactose = milk sugar = gluc + galact (β1,4)

4. Melibiose = broken down raffinose = gluc + galact

5. Raffinose = starch, beet, seed = gluc + galact + fruc

6. Stachyose = soybeans, jasmine,lentils = 2 galact + fruc

Glucose + Glucose disaccharide examples (5)

1. Nigerose = gluc gluc (reducing, α1,3)

2. Trehalose = zombie sugar = gluc gluc (nonreducing, α1, α1)

3. Cellobiose = gluc gluc = hydrolysis of cellulose

4. Gentobiose = gluc gluc = plant glycosides, amygdalin

5. Isomaltose = gluc gluc = hydrolysis of glycogen, amylopectin

Polysaccharides: energy reserve in plants.

Starch

Glucose (α-1,4 and α-1,6)

Made 80% amylose (spiral) and 20% amylopectin (branched)

Polysaccharides: energy reserve in animals.

Glycogen

Glucose (α-1,4 and α-1,6)

More branched than amylopectin

Polysaccharides: provides rigidity in plant cell walls.

Celluose

Glucose (β-1,4 linkages)

water insoluble

Differentiate polysaccharides: chitin, alginic acid, carrageenan, pectin

Percentage of starch

80% amylopectin, 20% amylose

Polysaccharide used as a stabilizer and gelling agent.

Carrageenan

Humans can’t degrade cellulose, because we don’t have the enzyme: ____ found in ruminant animals like cows and goats.

Cellulase

Which of the following correctly describes the classification and structure of glucose? Aldopentose, aldohexose, ketopentose, or ketohexose?

Aldohexose

Percent during equilibrium of mutarotation of D-glucose α + β?

67% β
33% α
trace% open form of D-glucose

Which of the following are kinds of epimeric pairs?
a. galactose-mannose
b. galactose-altrose
c. glucose-mannose
d. glucose-altrose

c. glucose-mannose

During oxidation of aldoses, what are the two products that can form?

1. Aldonic acids (if mild oxidizing agents are used, 1 COOH)

2. Aldaric acids (if strong oxidizing agents are used, 2 COOH)

What is the formula for number of chiral centers?

2^n