CHEM140 Exam 4 Review

aldose

C1 is an aldehyde

ketose

C2 is a ketone

chiral

objects with nonsuperimposable mirror images

achiral

objects with superimposable mirror images

structural isomers

same molecular formula, different bonding arrangement

stereoisomers

chiral structures with the same molecular formula and bonding, different 3-D arrangement of atoms in space

enantiomers

stereoisomers that cannot be superimposed

diastereomers

stereoisomers that are not mirror images

chiral carbon

any C atom bonded to 4 different atoms/groups

epimers

differ at 1 carbon, not mirror images

anomers

epimers at the anomeric carbon, not mirror images

anomeric carbon

formed from carbonyl newly formed chiral carbon, ends up as C1 in Haworth structure

L isomer

OH is on the left of the penultimate carbon

D isomer

OH is on the right of the penultimate carbon

penultimate carbon

chiral carbon furthest from the carbonyl group

D-glucose

most common hexose, blood sugar, found in fruits, vegetables, corn syrup, honey

D-galactose

brain sugar, not found free in nature

D-fructose

sweetest carb, found in juice and honey

alpha isomer

OH is below on C1/C2

beta isomer

OH is above on C1/C2

mutarotation

each isomer converts to an open chain structure and back again, allows alpha/beta isomers to form

maltose

2 alpha-D-glucose molecules connected by an alpha(1→4) glycosidic bond

lactose

beta-D-galactose and alpha-D-glucose connected by a beta(1→4) glycosidic bond

sucrose

alpha-D-glucose and beta-D-fructose connected by an alpha,beta(1→2) glycosidic bond

starch

storage form of glucose in plants, composed of amylose and amylopectin

amylose

250-4000 alpha-D-glucose molecules connected by alpha(1→4) glycosidic bonds

amylopectin

up to 100,000 D-glucose molecules connected by alpha(1→4) glycosidic bonds, with branches of glucose molecules every 25 units connected to the main chain by alpha(1→6) glycosidic bonds

glycogen

up to 1,000,000 D-glucose molecules connected by alpha(1→4) glycosidic bonds, with branches of glucose molecules every 10-15 units connected to the main chain by alpha(1→6) glycosidic bonds

cellulose

D-glucose molecules connected by beta(1→4) glycosidic bonds aligned in parallel rows connected by H bonds between OH groups

saponifiable

contain ester or amide bonds, building blocks are fatty acids

nonsaponifiable

don't contain ester or amide bonds

fatty acids

long, unbranched carbon chain with a carboxylic acid group at one end

saturated fatty acids

contain only C-C single bonds, have high mps and are solid at room temp

lauric acid

12:0

myristic acid

14:0

palmitic acid

16:0

stearic acid

18:0

unsaturated fatty acids

contain 1+ C-C double bonds, low mp and liquid at room temp

cis isomers

have a “kink” in carbon chain, don’t stack as effectively, lower mp

trans isomers

straight chain structure, stack more effectively, higher mp

monounsaturated fatty acids

have 1 C-C double bond, properties similar to alkenes

palmitoleic acid

16:1 delta 9

oleic acid

18:1 delta 9

polyunsaturated fatty acids

have 2+ C-C double bonds

linoleic acid

18:2 delta 9,12

linolenic acid

18:3 delta 9,12,15

arachadonic acid

20:4 delta 5,8,11,15

essential fatty acids

fatty acids that cannot be synthesized by the body in adequate quantities, must be obtained from the diet

omega-3s

PUFAs with a double bond 3 atoms away from the terminal methyl group

omega-6s

PUFAs with a double bond 6 atoms away from the terminal methyl group

prostaglandins

hormone-like substances formed from arachidonic acid that affect blood pressure and muscle stimulation (cause fever, pain, inflammation)

leukotrienes

formed from arachidonic acid, affect inflammation and reaction to allergens

triacylglycerols

what fatty acids are stored as in the body, esters of glycerol and 3 fatty acids

glyceryl triearate

formed with 3 stearic acids, example of a simple triglyceride

simple triglyceride

all fatty acids are the same

mixed triglyceride

fatty acids are different

fat

triacylglycerol that is solid at room temp, usually from an animal source, contain more SFAs

oil

triacylglycerol that is liquid at room temp, usually from a plant source, contain less SFAs

hydrogenation

H atoms break double bonds to form single bonds

complete hydrogenation

forms brittle fat product

partial hydrogenation

forms soft, semisolid fat

saponification

fat is heated with a strong base to form glycerol and the sodium salts of fatty acids

micelle

a spherical structure with hydrophilic heads on the outside and hydrophobic tails on the inside

phospholipids

family of lipids similar to triacylglycerols, includes glycerophospholipids and sphingolipids

glycerophospholipids

glycerol forms ester bonds with 2 fatty acids and 1 phosphoric acid, phosphoric acid forms another phosphoester bond with an amino alcohol

hydrophilic head

contains ionized amino alcohol and phosphate group

hydrophobic tails

contain hydrocarbon chains of the 2 fatty acids

sphingomyelin

type of sphingolipid with the similar structure to glycerophospholipids, except it only has 1 fatty acid and glycerol is replaced by sphingosine

glycolipids

sphingosine derivatives that contain no phosphate group that have an attached carb that is a monosaccharide or a short chain of monosaccharides

cerebroside

glycolipid attached carb is a monosaccharide

ganglioside

glycolipid attached carb is a chain of monosaccharides

amino alcohols

found in glycerophospholipids, contain a hydroxyl group and an amino group

choline

a lecithin, HO-CH2-CH2-N+, N attached to 3 CH3 groups

serine

a cephalin, HO-CH2-CH(attached to NH3+)-C(=O)-O-

ethanolamine

a cephalin, HO-CH2-CH2-NH3+

lecithins

type of glycerophospholipid that contains choline, abundant in brain/nerve tissue, egg yolk, wheat germ, yeast

cephalins

type of glycerophospholipid that contains serine or ethanolamine, abundant in same things as lecithins

phosphatidylcholine

most abundant cell membrane lipid

steroids

contain a steroid nucleus

steroid nucleus

3 cyclohexane rings and 1 cyclopentane ring fused together and designated as A, B, C, D

cholesterol

one of the most abundant steroids in the body, produced in the liver from fats, carbs, and proteins, used to synthesize steroid hormones and bile salts, considered elevated at 200mg/dL

bile salts

synthesized from cholesterol in the liver, aid in digestion of dietary fats (triglycerides)

transport proteins

carry essential substances throughout the body

hormone proteins

regulate body metabolism and nervous system

enzyme proteins

catalyze biochemical reactions in the cells

contractile proteins

make muscles move

protection proteins

recognize and destroy foreign substances

structural proteins

provide structural components

storage proteins

store nutrients

glycoproteins

carbohydrate prosthetic group

lipoproteins

lipid prosthetic group

metalloproteins

metal ion prosthetic group

phosphoproteins

phosphate group prosthetic group

hemoproteins

heme prosthetic group

nucleoproteins

RNA prosthetic group

standard amino acids

the 20 amino acids found in proteins of living organisms

essential amino acids

9/20 of the standard amino acids that must come from diet because they cannot be synthesized in the body

alpha carbon

central carbon atom bonded to 2 alpha functional groups, an ammonium group and a carboxylate group, an H atom, and the R group

R group

distinguishes amino acids from one another

nonpolar amino acids

R groups are H, alkyl, or aromatic groups