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C ar bo h yd r at e s
C a r b o h y d r a t e s m a y b e d e f i n e d a s p o l y h y d r o x y a l de h y de s o r k e t o n e s o r
c o m p o u n d s w h i c h p r o d u c e t h e m o n h y dr o l y s i s . T h e t e r m ' s u g a r ' i s a p p l i e d t o
car b o h ydr at e s s o lu b le in wat er an d s we et t o t as t e .
f u nc t i o n o f C ar b o h yd r at e s :
C a r b o h y d r a t e s p a r t i c i p a t e i n a w i de r a n g e o f f u n c t i o n s :
1 . T h e y a r e t h e m o s t a b u n da n t d i e t a r y s o u r c e o f e n e r g y ( 4 C a l / S ) f o r a l l
o r gan i s m s .
2 . C a r b o h y dr a t e s a r e p r e c u r s o r s f o r m a n y o r g a n i c c o m p o u n d s ( f a t s , a m i n o
acids ) .
3 . C a r b o h y dr a t e s ( a s g l y c o p r o t e i n s a n d g l y c o l i p i ds ) p a r t i c i p a t e i n t h e
s t r u ct ur e o f ce ll m em b r ane and ce llular f u nct io n s s uc h as ce ll g r o wt h ,
adhe s io n an d f e r t iliz at io n .
4 . T h e y ar e s t r uct ur al co m p o n en t s o f m any o r g an is m s T h e s e inclu de t h e
f ib e r ( cel lu lo s e ) o f p lant s , e x o s k e le t o n o f s o m e ins ect s an d t h e ce llwall o f
m ic r o o r g anis m s .
5 . C a r b o h y dr a t e s a l s o s e r v e a s t h e s t o r a g e f o r m o f e n e r g y ( g l y c o g e n ) t o
m e e t t h e i m m e d i a t e e n e r g y de m a n d s o f t h e b o d y .
C L A SSIFI C AT IO N O F C AR BO H Y D R AT E S:
C ar b o h ydr at e s ar e o f t e n r e f e r r ed t o as s acc h ar ides ( Gr e ek : s ak ch ar o n
- s u gar ) . T h e y ar e b r o ad l y cl as s i f i e d i n t o t h r e e m aj o r g r o u p s m o no
s ac ch ar ide s , o lig o s acch ar ide s and p o lys acch ar ide s .T h is cat eg o r iz at io n is
b as e d o n t h e nu m b e r o f s u gar u ni t s . Mo n o - an d o l i g o s acch ar i d e s ar e s w e e t
t o t as t e, cr ys t alline inch ar act er an d s o lub le in wat e r , h e nc e t h e y ar e
chemistry/second stage Lecture no.1
co m m o nly k n o wn as s ug ar s .
Mo n o s ac ch ar i d e s
O l i g o s ac ch ar i d e s :
P o l ys ac ch ar i d e s
i f t w o m o n o s a c c h a r i d e s di f f e r f r o m e a c h t h e r i n t h e i r c o n f i g u r a t i o n
chemistry/second stage Lecture no.1
E p im e r
G l y ce r al d e h yd e :
G l y c e r a l de h y de ( t r i o s e ) i s t h e s i m p l e s t m o n o s a c c h a r i d e w i t h o n e
as y m m et r icc ar b o n at o m . L t ex is t s as t w o s t er e o is o m e r as n d h as b ee n
ch o o s e n as t h e r e f e r en ce car b o h ydr at e is r ep r e s en t t h e s t r uct ur e o f all o t h er
c a r b o h v dr a t e s .
chemistry/second stage Lecture no.1
D " an d L - is o m e r s
T h e D an d L is o m e r s ar e m ir r o r im ag e s o f e ach o t h er . T h e s p at ial
o r i e n t a t i o n o f - H a n d- O H g r o u p s o n t h e c a r b o n a t o m ( C s f o r g l u c o s e ) t h a t i s
a d j a c e n t t o t h e t e r m i n a l p r i m a r y a l c o h o l c a r b o n de t e r m i n e s w h e t h e r t h e
s ug ar is D - o r L - is o m e r .o f t he - O H g r o u p is o n t he r ig ht s ide, t h e s ug ar is o f D
- s e r i e s , a n d i f o n t h e l e f t s i de , i t b e l o n g s t o L - s e r i e s . T h e s t r u c t u r e s o f D - a n d
L - g l u c o s e bas e d o n t h e r e f e r e n ce m o n o s acc h ar i d e ,
D - a n d L - g l yce r a l d e h yd e ( g l yc e r o s e ) a r e d e pi c t e d i n Fi g . 2 . 1. I t m a y b e n o t e d
t h at t h e nat ur ally o ccu r r ing m o no s ac ch ar ide is n t h e m am m aliant is s ue s a
r e m o s t l y o f D - c o n f i g u r a t i o n T .h e e n z y m e m a c h i n e r y o f c e l l s i s s p e c i f i c t o
m e t ab o lis e D - s er ie s o f m o no s ac ch ar ide s .f n t h e m edical p r act ice , t h e t e r m
d e x t r o s e i s u s e d f o r gl u co s e i n s o l u t i o n. T h i s i s b e cau s e o f t h e
de x t r o r o t at o r y nat ur e o f g lu co s e .
A l do s e s a n d k e t o s e s :
A c a r b o h y d r a t e i s c o m p o s e d o f c a r b o n ( c a r b o - ) , a n d h y dr o g e n a n d
o x yg e n
( - h y d r a t e ) . T h e s i m p l e s t c a r b o h y dr a t e s a r e t h e m o n o s a c c h a r i d e s t h a t h a v e
chemistry/second stage Lecture no.1
t he
g en er al f o r m ula ( C H 2 O ) n wh er e n is 3 o r m o r e . A m o no s acch ar ide o r s im p le
s u gar , co n s i s t s o f a c ar bo n ch ai n w i t h a n u m b e r o f h yd r o x yl ( O H ) g r o u ps and
e it h er o n e alde hyde g r o up ( o f t e n w r it t en as – CHO ) o r o ne k et o ne g r o up . A
s ug ar t h at b e ar s an alde h yde g r o up is calle d an aldo s e wh er e as a s u g ar wit h
a k et o n e g r o u p is a k e t o s e . T h e s m alles t car b o h ydr at e s , f o r wh ich n = 3 , ar e
ca l l e d t r i o s e s . T h e t e r m s ca n b e co m bi n e d . T h u s g l yc e r a l d e h yd e ( Fi g . 1) i s a
t r i o s e t h at h as an al d e h yd e gr o u p and s o i s an al d o s e . T h u s i t can al s o be
c a l l e d a n a l d o t r i o s e . S i m i l a r l y , di h y d r o x y a c e t o n e ( F i g . 1 ) i s a k e t o t r i o s e .
R ing s t r u ct u r e s :
T h e alde h yde o r k et o n e g r o u p c an r e act w it h a h ydr o x yl g r o up t o f o r m
a c o va l e n t b o n d . F o r m a l l y , t h e r e a c t i o n b e t w e e n a n a l de h y de a n d t h e
h ydr o x yl g r o up o f a s ug ar ( an alco h o l) cr e at e s a h em iace t al ( E q uat io n 1 )
w h e r eas a k e t o ne r eac t s w it h a h ydr o x yl g r o up ( alco h o l) t o f o r m a h e m ik e t al
(E q uat io n 2 ) .
s am e
m o lec ule s o t h at t h e s t r aig h t - c h ain f o r m o f t h e s ug ar cy cliz e s . Fo r e x am p le,
Fi g . 5 s h o w s t h e cycl i z at i o n o f D - g l u co s e t o f o r m a s i x - car b o n r i n g. T h e r i ng
s t r u ct u r e s s h o w n i n F i g. 5 ar e cal l e d H aw o r t h pr o j e ct i o n s i n w h i ch t h e p l ane
o f t h e r i n g c an b e i m ag i ne d as ap pr o x i m at e l y p e r p e nd i cu l ar t o t h e p l ane o f
t h e pap e r w i t h t h e t h i ck l i ne s o f t h e r i n g i n t h e d i ag r am po i nt i ng t o w ar d s t h e
r e a de r .
D i s a c c h a r i de s :
Su gar d e r i vat i ve s
T h e h yd r o x y l gr o u p s o f s i m p l e m o no s ac ch ar i d e s can b e r e p l ace d w i t h
ot he r
g r o u p s t o f o r m a r a n g e o f s u g a r d e r i va t i ve s . F o r e x a m p l e ,
p h o s ph o r yl a t e d s u g a r s s u c h a s g l u c o s e 6- p h o s ph a t e ( Fi g . 9 ) a r e i m p o r t a n t
m e t ab o l i t e s i n gl y co l ys i s
( T o pi c J3 ) . I n am i n o s u g ar s , o ne o r m o r e h yd r o x yl g r o u p s ar e e ac h r e pl ac e d .
chemistry/second stage Lecture no.1
R e f e r e n ce s :
1-instant_notes_in_biochemistry_2nd_edition by B.D. Hames & N.M. Hooper.
2 - L i p p i n c o t t ’ s I l l u s t r a t e d R e vi e w s : B i o c h e m i s t r y ; F i f t h E d i t i o n R i c h a r d A .
Har vey, Ph D &D en is e R . F er r ie r , P hD .
3 - B io ch e m is t r y __Sat yan ar ayana_ C h ak r ap ani