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Lipids

Fatty acids with <14


and >20 C are
uncommon

Fatty acids double


bonds have always
the cis configuration

30° bend in the


hydrocarbon chain,
pack less efficiently

Van der Waals


interactions
decrease melting
points
Lipids

ω6
ω3
Triglycerides

Most abundant

Energy reservoirs

Less oxidized than carbohydrates and proteins, thus yield


more energy upon oxidation

Anhydrous, whereas glycogen binds twoce its weight of


water. Fats provide six times more metabolic energy than
an equal weight of hydrated glycogen

Stored in adipocytes in adipose tissue, a subcutaneous


layer and in the abdominal cavity.

Fat content 21% in men and 26% in women, allows one to


survive until 3 months (glycogen less than day)
Phosphoglycerides
Amphipathic, nonpolar aliphatic and polar phosphoryl heads

Ester linkage
Phosphoglycerides
Phospholipases
Plasmalogen

Ethanolamine, choline or serine

Ether linkage

Easily oxidized, therefore act as sink for oxygen free radicals


Sphingolipids
Amino alcohol derivatives

Trans
config.

C18 amino alcohol N-acyl fatty acid


derivative of
sphingosine

A ceramide of myelin sheath


Sphingolipids
Cerebrosides/Glycosphigolipids: Ceramide with
head groups of a single glucose or galactose sugar
residues
Lack phosphate groups thus are nonionic

Gangliosides: Glycosphongolipids
Components of cell surface membranes,
constitute 6% of brain lipids
Carbohydrates act as receptor of pituitary
glycoprotein hormones, cholera toxin
Sphingolipids are a source of smaller
lipids that act as signaling molecules
Steroids

30-40 mol % of plasma membrane lipids


Weakly amphipathic
Fused ring system make it more rigid
Cholesteryl ester
Cholesterol is metabolic precursor for steroid
hormones
Glucocorticoids (Cortisol) and Mineralocorticoids
(Aldosterone)
Sex hormones: Androgen (testosterone) and
estrogens (β-estradiol)
Steroids
Vitamin D
Hormones or vitamins

Active Vitamin D

Vitamin D promotes intestinal absorption of


serum calcium
Vitamin D deficiency
Vitamin D intoxication
Other lipids

Plant pigments: Terpenoids Reversibly reduced and oxidized

Plants

Vitamin K

Retinol: Vitamin A from β-carotene


Retinal: Photoreceptor at low light
Retinoic acid: Hormone-like, tissue repair Bacteria
Other lipids

Anti oxidant

Eicosanoids (C20): Prostaglandins


Production of pain and fever
Arachidonate stored in membranes
Lipid bilayer
Lipid bilayer

Liquid Crystal Gel-like solid

Transition temperature increase with increase in hydrocarbon chain length,


cholesterol content
Cholesterol does not form bilayer and thus inhibits ordering of lipids
Membrane Proteins

Human erythrocyte glycophorin A


Membrane Proteins
Almost all membrane proteins are partially exposed to the aqueous environment

α-helices and β-barrels

Bacteriorhodopsin Porins
Lipid Modification of Proteins
Prenylation: Farnesyl and Geranylgeranyl made from Isoprene

Prenylation occurs of cysteine of C-X-X-Y via a thioester linkage

Myristoylation (by a C14 fatty acid myristic acid) α-amino group of an


N-terminal Glycine

Palmitoylation (by a C16


fatty acid palmitic acid) of
Cys for reversible
association to plasma
membrane