Quick

Repaso
 Repaso : Lipidos (Dado por profesor Dr(1G).

Lipids
· :

chemically diverse compounds

·
insoluble in water
·

soluble in [disolventes organicos]

·
oil, manteca , beeswax, zanahorias /Como pigmentos)
Lipids insoluble in water because non-polar
are
they are
·
.

They lack
charged groups ,
so the water molecules can't attach to
most parts of a lpid

Lipids excellent compounds for

energy storage because
·
are :
r

Lipids carry less water because they are nonpolar

Fatty acids store longterm energy
·

Fatty acids carry more energy per carbon because

they are more reduced
(when a molecul is reduced , it gains It electrons , making the molecule
gain energy in the process
·
Functions of Lipids :

·
intracellular messengers (involved in diferenciacion, division celular apoptosis etc) , ,

·
intracellular signals and redox factors (lipid Oxidation generates harmful products
,

·
membrane components (liposomas) lipid signaling in Liposomes of cells)
·
cofactors for enzymes

pigments
·

antioxidants

Fatty acids
·

Hydrocarbon derivatives
·

Fats' Oils used as stored

energy are derivatives of fatty acids
·

·
saturated and unsaturated Fatty acids :
saturated Fa
unsaturated fa= does doesn'thave double bonds
double bonds

Fatty acid nomenclature

·

The chain
length
and number of bonds , separated
by colon
·

Numbering begins at
carbonyl carbon
·

positions of double bonds indicated superscript number

are
by and a

monosaturated
#I assigned to carboxyl carbon
"Site of double bond
PUFA alternative
# assigned to terminal methyl carbon
colomega) - n =
site of double bond

·
20C Elkosi = zu
·

&
5 double bonds positions
 Physical properties of fatty acids
·

↑
chain I melting point
·
N chain , ↓ solubility
length Length
I solubility a double bonds
,↓
I chain length melting point, 4 double bonds

Importance of co-3 and co-6 fatty acids

·

c-3 and co-6

fatty acids function normal growth
role in brain
play a crucial
·

. Helps stimulate hair, bor strength

and development , regulate metabolism and maintain reproductive system
14 ,
17) EPA Can omega-3 acid) (fish oil
<. 8 ",
·

Example : 20 : 5) ,

Tricylglycerols (storage lipids

·

Tricylglyceros
-

simplest lipids constructed from fatty acids

in an ester linkage with 1
3
fatty acids glycerol
·

·
simple /I type of fatty acid) or mixed (2-3 different fatty acids)

hydrophobic non-polar
·

less dense than water

can be broken down to their component fatty acids and
glycero, which can be used as a source of the
body
energy by
solids = fats ; liquids = oils
·
stored in adiposito

·
Membrane
Lipids
Amphipathic molecules with both hydrophilic and
molecules are
hydrophobic parts
·

·
ceramicide (sphingosine + amide-linked fatty acid) + phosphocholine attached to the alcohol
-

abundant in sheath that surrounds some

Sphingomyelin myelin cells in animals
·
-
newe

Gangliosides have oligosaccharides as their polar head groups and It residues of

·
-

N-acetylneuraminic acid (Neu5AC)

, a sialic acid ,
at the termini
I Sialic acid residue =
GM (mono) series
-

GD (di) series
Isialic
acid residues
-
=

sialic acid residues : GT (tri) series

·
Cerebosides -
have a
singular sugar linked to ceramide
those with galactose are found in the plasma membrane of cells in neural tissue
those with in the plasma membrane of cells in non neural tissues
glucose are found

Globosides-glycosphingolipids with 2+ sugars usually D-glucose D-galactose or

·
,

N-acetyl-D-galactosamine
No charge & 7 pH
·
en la endosymbiosis
de la Mitochondria
 Glycosphingolipids determine blood
groups
·

Determined in
by type of sugars located
the the
groups glycosphingolipids
head
·
on

Ogroup no active glycosyltransferase

-

A group-glycosyltransferase transfer to N-acetylgalactosaminea

B group-glycosyltransferase transfer to
galactose
a

Biologically active lipids can serve as cell

signaling molecules
·
Ecosanoids -

paracrine hormones that act only on cells near the point of hormone synthesis
instead of cells in other tissues
being transported in the blood to act on or
organs

(PG ,
Prostaglandins Scarbon
ring) Some stimulate the contraction of smooth musch of
· -

the uterus
(PG) during menstruation and labor Others affect blood flow walksleep cycle
.
,

andresponsiveness of certain tissues and muscles

Cause temperature rise and cause inflamation + pain

Tromboxanos-6 membered ring containing an ether Produced

by platelets (thrombocytos
·
.

(TX) and act of blood clots and reduction of blood flow to the
in the
formation
site of the clot

Leukotrienes -
Induces contraction of the smooth muscle lining the airways to the
lung
(LT) Overproduction causes asthma attacks

Steroid hormones such as estrogen and testosterone are derived from cholested

·
Vitamin A 3D are fat-soluble isoprenoids that are precursors to hormones

·
Lipid analysis is difficult because its insoluble in water
Their extraction involves of solvents
organic
·
use
·
Mass spectrometry is
required for complete structure determination

Lipidomics-study of the structure and function of the

·

complete set of Lipids Clipidome) in a given

cell and its organisms as well as their interactions
with other
organisms
Ejs. Lipidos :
1) 20 : 0 eicosanoic acid (saturated)

0
M
%
18 : 1 (4 1 cis-9-Octadedonic acid
8

·
kom
2) Land is made out of
fatty acids,
which are not soluble because
they are non polar

3) Because it is an unsaturated acid

with one cis bond meaning it has
,

a lower melting point

4) Triacylglycerols are better storage than carbs .

because
theya reducing Ccan get more energy
and are insoluble in water
Ialso lower ammount of oxygen

5) Partial consists of
hydrogenation adding
hydrogen atoms (H2) to cis fatty acids
,
reducing them to be saturated or

into trans configuration

6) cisFA trans FA
keeps Fatty acid "Straight"
-
·
·
creates Kinks
unhealthy
·
·
heather
uncommon in nature
·

Common in nature
·

·
Raise HDL Cholesterol ·
Raises LDL cholesterd
·
Easier to break down
·
Harder to breakdown

7) Because storage FAs are hydrophobic while membrane FAS are amphipathic

8) GlyceroLipids are deratives of phosphatic acid

9)
Nonpolar

10) Perhaps their resistance to phospholipases that clave ester linked fatty acids
from membrane lipids is important in some roles

11) galactolipids sulfolipids

·
has phosphate ·
Lacks phosphate
·

diacylglycerol with 1-2 linked ·

sulfonated glucose is joined to a diacylglyend
galactose residue ina glycosidiz
Linkage
charge negatively charged
·
·
no

12) The glycer tetraethers bonds there since hydrolisize at pH

are
they're more stable to low

13) phosphocholim is the polar part of sphingomyelin

(4) Although similar

,

Diacylglycero has esther bonds

while ceramide is in an

end form and has an

amide

15) Lysosomes are important as they degrade material from outside the all to digest the obsolete
components from the cell itself and is where lipids are degraded

16) Stends have many rings instead of acids fatty

steros have a polar area and non polar side chains

17) Isoprenes carry electrons in redox R in ATP synthesis in Mitochondria and cloloplast
[12
I
(Hz = c - Ch = CH2
18) Phospholipases degrade phospholipids
Since most cells continually degrade and replace their membrane lipids
impaired by
When
degradationof is a
defect enzymesin the
,
there is a buildin lipids in
lysosomes a dysfunction
,

categoried as "lysosomal storcar disorders"

affector kids in "Orphan diseases"

19) Ibuprofen (Advil) reduces pain by inhibiting COX ,

an
enzyme that catalyzes the
initial steps of converting archidonate and and
tromboxane
prostaglin

20) Steroid hormones are carried through the body in the bloodstream ,
usually
attached to carrier proteins

2) Vitamin A
Piel ojos
y membranas mucosas resecos
·

retraso en desarrollo
·

·
problemas de vision

Vitamin D
·
defectos en formacion de nueso raguitismo
y
22) Platalets Activating Factors :
-

Senal molecular
muy potent
secretada por leucocitos para estimular agregacion de
plaqueta
importante en la inflamacion y respuestas alergicas (intervenir)
Stimulates of blood platatr
aggregation
Repaso : Carbs ·
(Dado por profesor Dr C1G)
.

Monosaccharides are monomeric subunits from subunite from which

· which
oligo and
polysaccharides
-

are formed

They're classifiedaccordingto
· :

or Ketore)
1) The position of the carbonyl group Caldehyde
2) Total # of carbon atoms in the chain (triose pentose , nexosel
,

i
3 Isomeric form (LorD)
Wether or not they occur in cyclic form
they have another chemical substituent
C Wether or not
6) Nomenclature
7) proper conversion fischer > cyclic form -

·
Basic nomenclature:
·
Formula : Cn(H20) n

·
monosaccharides , disaccharides , polysaccharides
·
# of Catoms + osalose
·
3C = triosal triose
·
4C = tetrosa/tetrose
·
SC = Pentosa/Pentose
·
6C = Hexose/Hexosa
·
7C =
Heptosa/Heptose
·
Common functional groups
·

aldehidos/aldehydes-" Aldopentosa/aldopentose" aldehyde functionality

·
utonas/Ketones -

Utopentosa/Ketopentose" Ketone functionality

·
A molecule w/ n chiral centers can have 2" stereoisomers
Epimers are diastomers of I that differ configuration of 1 atom
sugars
·
in

Most monosaccharides exist as cyclic structure

Aldehyde and Ketone carbons are electrophilic
·

Alcohol oxygen is nucleophylic

·

When is attacked by alcohol they

form
·
:

aldehyde ; hemicetals
Ketona ; hemiketals

Pyranose
·

6 membered ring compounds

Form when the C5 reacts with the Keto at C
hydroxyl group group
·
Furanose
5 membered
·

ring compounds
Form when the
hydroxyl group at C5 reacts with the Keto
group at C2
Cyclization of monosaccharides
Pentoses and hexoses easily undergo intramolecular
cyclization
·

Most common form in water

The former carbonyl carbon becomes a new chiral center as a
hydroxyl group
called the anomeric carbon
If the hydroxyl group is on the opposite side (trans) of the ring as the

CHzOH the configuration is G

If the the same side (cis) of the CHzOM,
hydroxyl group is on
ring as the

the configuration is B

is
anomeric carbon : carbon in
sugar that
an ketone in the open-chain
aldehyde or
and becomes a streocenter in
form
form
the cyclic

Haworth
perspective formulas
:

clockwise direction anomeric carbon

Number the carbons in a
beginning with the ,
then placing the
hydroxyl groups
it is placed
If the -OH group is to the pointing down
right ,
If the-OH group is to the left it is placed up pointing
The terminal CHzOH projects upward for the D-enantiomer
group ,
·

downward for the -enantiomer

The on the
hydroxyl
:
anomeric carbon can point up and down
same side of the rings as Co its B (Cis)
·
opposite side of the rings of Co its & (trans)

its his
·

Polysaccharide vary in monomeric composition , type of glycosidic bond connecting the monosaccharide
units, chain of and biological function
length and degree , branching
1) Starch (in plants) and
glycogen Canimals) are homopolysaccharidesthat function as fuel
storage
2) Starch and glycogen are chains of monomers connected by their linear linkages (2-4)
glucose
but with different
degree of branchingthrough (6) glycosidic bonds
3) Cellulose is also a
homopolymer of glucose but its (B1-4) linkages result in rigid extended
,
polymers
by cells for support rather than energy storage
used
4) More complex hetero polysaccharides can be covalently cross-linked to form
by peptides or proteins
peptidoglycans or proteoglycans
5) These carbohydrate protein aggregates function to provide support (cell wall),
-

connectivity (extracellular matrixs ,

among others

Glycoconjugates include
· :

Proteoglycans
important components of extracellular matrix of multicellular animals
·

composed of glycosaminoglycan chains that are connected to a protein are important for structure
Glycoproteins
·

Contain smaller diverse linked to aminoacid residues via O - or

oligosaccharides N-glycosidic bonds
·
more
,

Glycolipids
·

·
Lipids that are covalently bound to oligosaccharidy moieties

1) ·
aldose is a carbohydrate with aldehose functionality
·
Ketose is a carbohydrate with Ketone functionality

4) No
CH20H

t
5) B-D-glucose
CHA
H on

N Ho H

crizon

2) Stereoisomers -
2+ compounds
differing only in the spatial arrangement of their atoms
Enantiomers type of stereoisomer thatc re nonsuperimposable mirror
-
- a images
Diasterasomers-stereoisomer that aren't mirror
images
Epimers- Type of diastomer in where I sugars differ only in the
configuration of I atom

3) Basic nomenclature :
·

#of Catoms + osclose

3C = triosa/triose
·

·
Common functional groups :

aldehydes/aldelidos "aldopentose/aldopentosa" has

=
aldehyde functionality
Ketones/Atonas = "Ketopentose/cetopentosa" has Ketone functionality
-
 CHzON
CUzOn
6) nocke O fructosa c = 0

U
M W
H HO

on on

1) Se forman hemicatonal

8) Give rise to polysaccharides

9)
Phosphorylationofsugarsisimportantsincetheytrapsugars insidethe
a
10) reducing sugars are ends of disacchirade chains with a free chomeric carbon