Lipid structure and function

TRUE LIPIDS o I ,---, H-C-Oj-I

are esters of fatty acids and alcohols, formed by condensation their insolubil ity in water.

reactions.

Many of their properties result from

Water-repellent properties: oily secretions of the ,.,b,1('['(II" 1'1,111<1, hrlp tn w.ucrproof the iur ,111d skin. TIlE' 1"('l'l1 gl,)I,d (If bird, prncilllC5 ,1s~'uelioll which performs ,1 ,ill,il,)I' fllll( liol1 <)11 iho iE',lIh'r5.

I /--- -- .: , ~ H-C-Oj-I Hq-C---t!yO~o~.~ I --- -- -- C---BS':~~o9E H- c-Oj-I HO,~ENBJ

/ '\

II HO/C-lB:y?~oQ~~@

o 0 I II H-C-O-C---t!vO~O~CH) H-C-O-C~

I I

~ .

-- - -

II

H GLVCEROL

0 3FATIVACIOS

3H,0

H-C-O-C~ I II
H 0 TRIGL VCERIOE

Since the hydrocarbon chains are long (19 C in arachidonic acid) most of the weight of the triglyceride is fatty acid.

-~,

Cell membranes: I'hn<phnlipid5 (phosphatides) <lIT'found in .111 n'll memhranes. These molecules have ,1polar l,ho'l'h;1IP-h,I<(" woup substituted ior one of the fatty acids iu ,1trigkcrricil'. This part of the molecule
r-

----.,

Waterproofing: the waxy cuticle of insects and plants reduces water losses by evaporation since water cannot cross the insoluble lipid layer. Waxes are esters of higher fatty acids with long chain alcohols (i.e. 1101 with glycerol).

is very insn!lIiJ1e in water

Thi< part of the molecule i< verv ~()llIhle in water

"".

"-+.

'1

ORGANIC' BASE

PHOSPH"T~-

---------.---. ---------01---

Storage: high energy yield per unit mass and insolubility in water make fats and oils ideal energy storage compounds, particularly where dispersal or locomotion requires mass to he kept to <Iminimum, <IS in some seeds and fruits.

~lectriCal insulation: mvolin is secreted by Sr hwann cells ,llld ill<lIl,II('< somo [)('UI'IlIlf'S ill S\I( h ;'I W;'Iy Ih;'ll impulse [ 11,1I1Smis5ion m,ld~' 1I1uch more rapid. i5

-----------------------,

,D

D-

~ .,
t>J\SIC STEROID NUCLEUS

Hormones: an important group of hormones, including cortisone, testosterone and oestrogen, Me steroids. Steroids are not true esters hut have the same solubility properties .15them .

ro
OJ

::J
::J

DC

-PhYSiCal protection: the shock-abvorhing ahilitv of <uh, ul.1I11:'0u< <;Iorp<protects delicate (lrgan5 such .15thE' 1',11 k.idlle\'5 Irom mechanical damago.

----------------------------~
Thermal insulation: f;'lts conduct heat very poorly <uhcutaneous iat stores help heat retention in endothermic .mimal. lnrompressible blubber is <In important insulator in diving mammals.

DO

::J

Nutrition: both bile acids and vitamin 0 (involved in fat digestion and Ca2+ absorption respectively) are manufactured from steroids.

Honeycomb: bees use wax in constructing their larval chambers.

0)

c ::J
(5
Ul

11

Sl
:::l

Functions of soluble carbohydrates include transport,

protection, recognition and energy release.
Sugar derivatives include sugar alcohols, e.g. glycerol, sugar acids. e.g.

Glucose is the most common substrate for respiration (energy release). Fructose is a constituent of nectar and sweetens fruits to attract animals and aid seed dispersal.

In naturally occurring glycosidic bonds.

disaccharides

monosaccharide

rings are joined together by

S,
Ul

ascorbic acid. and

/ll(/COPOII'9ccharides, which are important COIllPonen~5 of connectivE' tissues. <vnovial fluid. (Mtil,lgp and hone. Hep,1I in I,ln!i("(),lgul,lnt in hlood! i< df'ril"('d from
.

0-

This most usually occurs between aldehyde or keto group (i.e, the reducing group) of one monosaccharide and an hydroxyl group of another monosaccharide, e.g. lactose

m o
OJ ....

0-

~,

'< o.

o zr
QJ co
Ul

Glucose and fructose are both monosaccharides (single sugar units) with the typical formula CnH2"0,,. They each
BATS LIKE IT RUNNY'

1ll1l("llplll\'~,1Ct h,lritics ,1Ild has ,1 protect ive 1\II1C!on. i

have six carbon atoms and are thus called hexoses tpentoses have S carbon atoms and trioses have ]). Glucose and fructose are isomers of C(,H 120r,'
CH,OH

IG,~ro"J>$
'<,

"

Reducing group of galactose

Hydroxyl group on C4 of glucose

Oligosaccharides are short (often 6t ~ units) condensation products which combine with protein (glycoprotein) or lipid igivcolipid: and form the outer cnal I.g/Icocal\"\! of animal cells. They .ire important in cell-cell recognition .ind the imlllune response.

Reducing group of glucose = carbonyl group (C=O)

C~H'OH

CH,oH

(Maltose is a reducing disaccharide

OH

formed from two molecules of a-glucose.)

H
aGLUCOSE H OH

H
(lFRUCTOSE

or, more rarely, between reducing groups of odiecent monosaccharides, e.g. sucrose

~
Reducing groups are joined

Ribulose bis phosphate is the ecceptor of CO! in the Calvin Cycle.

Ribose and deoxyribose are constituents of nucleotides

o
co,
,/
Ru8P CALVIN CYCLE 'FIXES' TRIOSE SUGAR

Other important roles are in the electron carriers NAD, FAD and NADP and as the 'energy currency'.

Sucrose (glucose-fructose) is the main transport compound in plants. Commonly extracted from sugar cane and sugar beet and used as a sweetener. Lactose (glucose-galactose) is the carbohydrate source for suckling mammals - milk is "bout S'X, lactose. Maltose igtucose-giucose; germinating seeds.

TATE & LYLE

ATP

co,

which are the subunits of nucleic acids

(e.g.

~o~.
~"CHAINOF ~ NUCLEOTIDES

LJ-1~~~=o

ADENINE

DNA).

is a respiratory substrate in

Starch

i< " Ini,turp

pi two pol\,l11Pr~ of rrgluco~(': amylose

lflll gllle(l,!> IInit~ joinr'ri hI'
(y

'\111. ,,11\ , . ,.l~in, .i" ~ {,h, " c i,I: . I ..... 1_

1.4

~olVsacehaMdes

.u c: uolvm=rs

Starch i5 a mixture of two polymers of a-glucose: amylose tvpirallv contains about 300 glucose units joined hy a 1.4

Polysaccharides
formed by glycosidic subunits

glvcosidic bonds

are polymers bonding of monosaccharide

Cellulose is a polymer of glucose linked by fJ 1.4 glycosidic bonds. The fJ-conformation inverts successive monosaccharide units so that a straight chain polymer is formed.

o
o l hc hulk" -CH/)H ~idE' chains cause the molecule to adopt helical shape (excellent for packing many subunits into a limned space).

/~

(//////

The parallel polysaccharide

I I I I I I I

chains are then cross-linked

by

hydrogen bonds.

/'

---

-, <, H

-,
\ \ I
/

/'

---

------

-, <,
\

I
Amylose helix (6 glucose units in each lurn)

OH \ \ I I I
H I'H CH,OH O'H CH'i

I
I
\ \

\ \ I~ I /
/ /

I I \ \
\ "/l-GLUCOSE <,

Amylopectin is a branched chain, containing up to 1500 glucose subunits, in which a 1,4 chains are cross-linked by a 1,6 glycosidic bonds.

,
<,
<,

OH
a-GLUCOSE
I-I I I

H
/

Hydrogen bonds ---~

./

...... ---1---

.-'

"0

V
,H ,
OH H H OH OH H

CH,o~H

I I I I I I
I I I I I

c/oof:/dvO
This cross-linking prevents access by water, so that cellulose is very resistant to hydrolysis and is therefore an excellent structural molecule (cellulose cell walls): ideal in plants which can readily synthesize excess carbohydrate.
CH, CH,

I I

rr 1.6 GL YCOSIDIC BOND

I I I I

CH,OH

<" (fJ
III

lJ

o
H OH H OH H OH

Glycogen is an a-glucose polymer, very similar to amylopectin but with very many more cross-links and shorter a 1.4 chains. This is appropriate to animal cells which may need to hydrolyse food reserves more rapidly than plant cells would do.

I
O=C O=C

Chitin

is another fJ

1,4 polymer - the

subunits in this case are amino derivatives of fJ-glucose called Nacetylglucosamine. It is another structural molecule abundant in arthropod exoskeletons and in fungal cell walls.

o o

III

tr

..,
CO
(fJ

0.:

Because there are so few 'ends' within the starch molecule there <Ire iE'\\' points to begin hydrolysis by the enzyme smvlese. Starch is therefore an excellent long-term storage

:t\

I
vCH'O~ H 0 OH H H H O=C NH H 0 ~H N:H OH H H 0 CH,OH 0"

"0

V
H OH H H H N-

CH'O~ ~H 0 H

N:H OH H H 0 CH,OH

I I

I I
C~

O=C

compound.

C~