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CARBOHYDRATES
N/A
51
Biochemistry
Undergraduate 3
10/31/2012

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Cards

Term
Carbohydrates
Definition
most abundant on earth; structural element of plant--cellulose 
Term
3 major groups base on their basic structure
Definition

simple sugars

complex carbohydrates

glycoconjugates

Term
simple sugars 
Definition

mono/disaccharides and polysaccharides

structural roles; storage form of glucose

sweet; used as additives to enhance flavors of processed food

Term
glycoconjugates 
Definition
carbohydrate units; glucose covalently bonded to protein=glycoproteins; glycolipids 
Term
glucose
Definition
most plentiful on monosaccharide in nature; polyhydroxy aldehyde (C=O inside the chain)
Term
Fructose
Definition
same molecular structure as glucose, but is a polyhydroxyl ketose (C=O is the first C in the chain)
Term
Enantimers
Definition
chiral compounds that lack a plane of symmetry and exist as two typical isomers--either L or D form 
Term
Monosaccharide
Definition

aldoses and ketoses

colorless, crytalize, soluble in H2O, insoluble in nonpolar solvents 

two asymmetric centers 

cyclic structures 

3-D structure is important in determining the biological function and properties 

linked by a condensation reaction, resulting in the elimination of h2o

Term
Anomers
Definition
isomeric forms thta differ only in their configuration about the hemiketal or hemiacetal carbon atom... alpha or beta anomers
Term
Epimers
Definition
sugars that differ only in the configuration around one carbon atom
Term
Aldose
Definition
two chiral centers (C1 and C6)
Term
ketose
Definition
three chiral centers (C1, C2, and C6)
Term
Monosaccharides as reducing agents
Definition
by measuring the amount of oxidizing agent reduces by a solution of a sugar, it is also possible to estimate the concentration of that sugar
Term
Functions of Carbohydrates
Definition

metabolic break down of monosaccharides provide most energy used to power bioological system processes

structural materials 

cell walls; connective tissues

signaling; cell-to-cell interactions 

 

Term
Effect of sugar phosphorylation in the cells
Definition

to trap the sugar inside the cell; most cells do not have plasma membrane transporters for phosphorylated sugars 

 

phosphorylation activates sugars for subsequent chemical transformation 

Term
Medical Analogy 
Definition

too low glucose =death, permanent brain damage

animals evolve hormonal mechanisms to ensure the concentration of glucose in the blood remains high enough

average glucose concentration can be assessed by looking at it's effect on hemoglobin; hemoglobin is constantly exposed to glucose at whatever concentration is present in the blood. 

 

Term
Disaccharides
Definition

contains glycosidic bonds

o-glycosidic bond formed when a hydroxyl group of one sugar reacts with the anomeric carbon of the other. 

 

glycosidic bonds are readily hydrolyed by acid, but resist cleavage by bases

Term
Naming Disaccharides
Definition

give the configuration (alpha or beta) at anomeric carbon joining 1st mono units on left to the 2nd

 

name non-reducing residue; insert "furano" or "pyrano" 

 

indicate in (  ) the 2-carbon atoms joined by glycosidic bond; with an arrow connecting the 2 numbers. 

Term
Difference in Carbohydrates
Definition

linkage 

enzyme is not present to break down glucose/sugars 

 

Sugars are lubricants for joints 

Term
Functions of Carbohydrates (2)
Definition
energy-fuel (quick energy); starch; glycogen; glucose; fructose; sucrose
Term
Structural Properties of Carbohydrates
Definition
cellulose; chitin 
Term
Signals (Carbs)
Definition
based on sugar linkage
Term
Structure
Definition

simple building blocks (Mono)

ketones or aldehydes (ketose/aldose) 

multiple OH groups 

Term
Fischer Projection 
Definition

OH and  H determine D and L

OH on right=D

OH on left=L

 

Term
Diastereoisomers
Definition

non-mirror image 

most oxidized carbon up; rest of the chain down; OH/H on sides 

smallest carbohydrates

aldehyde most oxidized = up 

chiral center

Term
Relationship between glucose and other sugars
Definition

D-glucose v. L-glucose

 

Term
Ketose
Definition

doesn't start at with chiral center b/c ketone is in the middle 

 

less branched

Term
Representation of Structures
Definition

in our bodies, structures don't exist linearly, but in rings 

our taste buds recognize linear structures but body cannot absorb them

Term
Pyranose
Definition

non-planar

2 chair conformation 

3-D conformations can determine function and biological properties of polysaccharides

Term

RING                                        LINEAR

Definition

UP (alpha)                                         LEFT (UP)

DOWN (beta)                                   Right (down)

Term
glycosidic bond
Definition
disaccharides aris through the formation of o-oligolycosidic bonds; condensation of anomeric carbon hydroxyl group with an alcohol
Term
Cyclic structure of glucose
Definition

in aqueous solution: 

>4 carbon backbone mono (ring)

carbonyl (aldehyde or ketone) O of hydroxyl of most last carbon 

aldehyde + alcohol=hemiacetal 

ketone + alcohol = hemiketal 

Term
Polysaccharides
Definition
Vary in: monomeric composition, type of glycosidic bond connecting the monosaccharide units, chain length and degree of branching, biological function, do not have definite molecular weight
Term
homopolysaccharide 
Definition
made from only one sugar type, heavily hydrated (many -OH), readily dissolve; storage-starch (in plants); glycogen (in animals); structural: cellulose (plant cell-wall); chitin (animla exoskeleton)
Term
heterpolysaccharide
Definition
made from more than one sugar type; extracellular support; peptidoglycan (bacteria cell envelop); extracellular matrix in animal tissues
Term
Glycogen 
Definition

extensively branched and compact thn starch. Why? degrading enzymes work on the non-reducing ends; more branched b/c more non-reducing ends; faster degradation

 

Term
chitin 
Definition
exoskeleton of anthropods; linear, unbranched homopolymer
Term
Amylase
Definition
breaks down starch 
Term
Anomeric Carbon (2)
Definition
binds two oxygens
Term
Polysaccharides (2)
Definition
  • storage(basic building block is glucose)
  •  starch-branched at every24-30 D-glucose
Term
Glycogen
Definition

animals (d-glucose) 10,000 or more 

alpha(1-4) linkage w/ alpha (1-6) branches

more branches 

more movement 

quick energy

found in liver and muscles: liver functions to maintain blood sugar levels; muscles uses glycogen

Term
Metabolism 
Definition

24 hours of sugar storage 

shortage of storage of glycogen 

no control over fat; but over glucose 

Term
STRUCTURE
Definition
Cellulose--accounts for about 1/2 the biosphere; makes up all the plant material.... cell wall, 90% cotton, 50% wood
Term
Cellulose Structure cont'd
Definition
linear polymer= beta (1-4) linkage (diff. btwn starch is the linkage); no branches in cellulose just linear; enzyme is cellulase--humans don't have this enzyme; can't use cellulose
Term
roughage
Definition

body can break it down or fiber 

soluble/insoluble fiber: need both

more fiber= more cholesterol

Term
Chitin
Definition

exoskeleton of insects, lobster, etc.

modified beta (1-4) linkage

Term
Carbohydrates (other functions)
Definition

glycoprotein: sugar attached to proteins 

side chains (serine) b/c of OH 

not anomeric; carbon amino acids break up sugars

Term
Glycolipids
Definition
phosphate head with OH
Term
glycoaminoglycans
Definition

found in joints; shock absorbers 

 

(fig. 7.9 in text)

Term
Relative sweetness factor
Definition

bar set by table sugar = 100%

dextrose (glucose) = 70%
maltose = 40%

galactose = 15%

fructose = 170%

lactose = 15%

honey is 40% fructose and remainder is glucose 

Term
High fructose corn syrup (HFCS)
Definition

corn; starch

ratio= 50:50 -fructose:sucrose

doesn't diff. much biochemically; can go unregulated in liver and create fat in liver; fruit juices in alcohol creates fat in the body

quite the same as sucrose, but there's a lot available since it's cheap, it can be easily accessed

heat changes aldose to ketose

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