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Carbohydrate Chemistry: Structure, Isomers, and Functions, Study notes of Biochemistry

Massachusetts College of Pharmacy & Health Sciences (MCPHS)Biochemistry

Carbohydrates: chemical formula, photosynthetic production, and size range. Functions include energy storage, structural roles, and cell signaling. Nomenclature, functional groups, and isomers (aldoses/ketoses) are explained. Stereoisomerism (enantiomers/epimers) is covered, with examples like d-glucose, d-mannose, and d-galactose. Useful for biochemistry/organic chemistry students, it introduces carbohydrate chemistry and its complexities. It aids understanding of structural diversity and functional roles in biological systems, providing a foundation for further study. Suited for high school and university students, offering a clear explanation of complex concepts.

Typology: Study notes

2022/2023

Available from 05/23/2025

asia-adams-lemar 🇺🇸

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Carbohydrates

Formula

_>Cn(

Hao

)n

Produced

by

CO

,

-11-1,0

via

photosynthesis

Range

→

small

(

glyceraldehyde

Mia

,

-

-90g

/

moi

)

+

◦

large

(

amylopectin

Mix

,

>

200,000,000g

/

MOI

)

Variety

of

functions

:

CHZOH

Energy

source

+

energy

storage

structural

component

lcellwaii

-

exoskeleton

)

µÉt[],tÑ

Informational

molecules

in

cell

signaling

H

OH

H

OH

covalently

linked

with

proteins

+

lipids

carbohydrate

Nomenclature

H

\

SO

1

Carbohydrates

__

Functional

group

-1

#

of

carbon

atoms

+

Suffix

C-

ose

)

C

M

-

&

-

OH

H

-

d-

OH

C=0

Basic

-7

#

of

carbon

atoms

in

carbs

-1

-

Ose

'

-10×9%0

I

1

H

-

C

-

OH

H

-

C

-

OH

1

Example

:3

carbons

__

those

H

common

Functional

groups

→

All

carbs

had

a

carbonyl

functional

group

Aldose

ketose

Aldehydes

-_

aldose

Carbohydrates

can

be

constitutional

Isomers

ketones

__

ketose

Aldose

-73

carbon

carbs

+

aldehyde

functionality

H

1

ketose

-73

carbon

carbs

+

ketone

functionality

H

CIO

CHZOH

I

1

I

H

KO

H

-

C-

OH

GO

H

1

I

1

I

H

0

I

14

H

GO

HO

-

C-

H

HO

-

C-

H

HO

-

C-

H

G

H

-

f-

OH

1

I

1

I

1

H

-

c-

OH

c=o

EO

H

-

C-

OH

H

-

C-

OH

H

-

C-

OH

H

-

C-

OH

1

I

1

I

1

I

1

H

-

C-

OH

H

-

C-

OH

H

-

C-

OH

H

-

C-

OH

H

-

C-

OH

H

-

C-

OH

H

-

C-

OH

1

I

1

I

1

I

1

H

CHZOH

0-1201-1

CHZOH

CTKOH

Glyceraldehyde

,

Dihydroxy

acetone

caido-riosejcke-o-rios.es

D-

Glyceraldehyde

D-

frythrose

Dttrabinose

D-Glucose

D

fructose

Aldose

Ketos e

Those

Tetrose

Pentose

Hexose

Aldotrlose

Aldotetrose

Aldopentose

Aldohexose

Ketoh exose

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Download Carbohydrate Chemistry: Structure, Isomers, and Functions and more Study notes Biochemistry in PDF only on Docsity!

Carbohydrates

Formula

_>Cn(

Hao

)n

Produced

by

CO

,

-11-1,

via

photosynthesis

Range

→ small (

glyceraldehyde

Mia

,

-90g

/ moi )

◦

large

amylopectin

Mix

,

200,000,000g

/MOI

Variety

of functions :

CHZOH

Energy

source +

energy

storage

structural component lcellwaii

exoskeleton

μÉt[],tÑ

Informational molecules in

cell

signaling

H OH H

OH

covalently

linked

with

proteins

lipids

carbohydrate

Nomenclature

H

\

SO 1

Carbohydrates

__ Functional

group

-1 # of carbon atoms

Suffix

C- ose)

C M

&

OH

H

d-

OH C=

Basic

# of

carbon

atoms in carbs

Ose

'

-10×9%

I 1

H

C

OH H

C

OH

Example

:3 carbons

__ those

H H

common

Functional

groups

→ All carbs had a

carbonyl

functional

group

Aldose

ketose

Aldehydes

_

aldose

Carbohydrates

can be constitutional Isomers

ketones

__ ketose

Aldose -73 carbon carbs

aldehyde functionality

H

ketose

-73 carbon carbs + ketone

functionality

H

CIO

CHZOH

I 1 I

H

KO

H

C-OH GO

H

I 1 I

H 0

I

14 H

GO HO

C-

H HO

C- H HO - C- H

G

H-

f-

OH

1 I

I 1

H

c-OH c=o

EO H

C-

OH H

C-

OH H

C-

OH

H

C-

OH

1 I

I

1 I

H

C-OH H

C- OH H -

C-

OH

H

C-

OH

H - C-

OH H

C-OH

H- C- OH

I

1 I

H H

CHZOH 0-1201-

CHZOH CHZOH

CTKOH

Glyceraldehyde, Dihydroxy

acetone

caido-riosejcke-o-rios.es

D- Glyceraldehyde

D- frythrose

Dttrabinose D-Glucose D fructose

Aldose Aldose

Aldose Aldose Ketose

Those Tetrose

Pentose Hexose

Hexose

Aldotrlose Aldotetrose Aldopentose

Aldohexose Ketohexose

Carbohydrates

Can Be

Stereoisomers

Enantiomers →stereoisomers that are

non

super imposable

mirror images

μ&E§Éld

¥

:

Sugars

contain

many

chiral centers ;

only

one is most distant from the

a

☒q¥%¥¥;¥¥¥

carbonsioarnoniaesisnaieaas

.in

.mn

⑤

L Isomers of

sugar

are enantiomers

CHzOH

dCH&Oft

Example:L and D

glucose

have the same water

solubility

Most hexoses in

living

organisms

are D stereoisomers

Otc

H

0+4-1-

H

{

OH HO

-42-1- Some simple sugars

occur 1hL form

HO

DEH H

-43-01-

HO

{

H H

C

L

arabinose D- Mannose

☐

galactose

lepimersof

D-glucose

H

¢-

HO

CEH

1

DMannosetbgalac-osecdlastereome.rs

CHZOH CHZOH

D-

Galactose 1- Galactose

'

CHO

'

CHO

'

CHO

HI-

OH H

- C- OH

Epimers

→ Stereoisomers that differ atone

1-10%-1-1 HO- C

H Ho-C-H

41

Chiral center ,

not mirror images ,

are diastereomers

4-4-

H

C- OH HO - .C - H

s

HIC-

OH 4-C-

OH HI

OH

1 I

Diastereomers →different

physical properties {

HZOH GCHZOH GCHZOH

Water

solubility

melting

temp

DMannose

D- Glucose

D-

Galactose

Cepimeratc

Cepimeratci

)

D Aldoses

D. Ketoses

3 carbons 4 carbons

5 carbons

Hypo Hyμ 0

Hyde

4 × 0 1-4× 0

{

,

3 carbons

carbons

CHZOH

Hypo

g

H

-4-01-

HO-

f-

H H

f-

OH

1-10-4-

CHZOH

, H-g-OHHO-o-HH-g-OHH-C-OHHO-j-HHO-i.tt

H-

f

OH

H- C

OH

H-q-OHH-yd-OHH-f-OHH-f-OHH-i.tt

'

H

f-

OH

HZOH

CHZOH

{

HZOH CHZOH CHZOH CHZOH CHzOH CHZOH CHZOH

Dihydroxy

acetone D Erythrulose

D Glyceraldehyde

D Erythrose

D-Threose D-Ribose D. Arabinose b- Xylose

D- Lyxose

s carbons 6 carbons

6 carbons CHZOH CHZOH

4 × 0 4,

9-

"

4=0 d=o

Hyo

4,0 Hypo

g

4 ¥

°

4 ¥

F-

°

+1-

OH

+10-1-1-

H-c-OHAO-d-HH-f-OHHO-C-HH-f-OHHO-g-HH-q-OHHO-c.tt

H -

I

°

"

1-1-

.

H-

f

OH

1-1-1- H

OH

OH

H-fc-OHH-f-OHHO-q-HHO-f-HH-f-OHH-f-OHHO-i.tt +10--4-1-

CHZOH

CHZOH CHZOH

H-g-OHH-f-OHH-f-OHH-f-OHHO-i-HHO-c-HHO-f-HH-i.tt

☐ Ribulose

ppsicose ☐

fructose

H-f-OMH-f-OHH-f-OHH-f-OHH-g-OHH-f-OHH-f-OHH-f-OHf.tk

OH 9-1201-

CHZOH CHZOH CHZOH CHZOH

CHZOH

CHZOH CHZOH

41-1201-

D- Aldose

pttltrose D Glucose DMamnosepfulosebldoseDGalactosep.la/ose 1 I

4=

H

- OH 1-10--1-

HO-

,

H

1-10-

H HO-

H

H

H

,

OH H -

OH H -

,

OH

CHZOH

CHZOH CHZOH

b Xyllllose

b sorbose

D. Tagatose

Carbohydrate Chemistry: Structure, Isomers, and Functions, Study notes of Biochemistry

Related documents

Partial preview of the text

Download Carbohydrate Chemistry: Structure, Isomers, and Functions and more Study notes Biochemistry in PDF only on Docsity!

Carbohydrates

Formula

_>Cn(

Hao

)n

Produced

by

CO

photosynthesis

→ small (

Mia

-90g

/ moi )

large

amylopectin

Mix

200,000,000g

of functions :

CHZOH

Energy

energy

storage

structural component lcellwaii

H OH H

OH

linked

proteins

lipids

H

\

__ Functional

group

-1 # of carbon atoms

Suffix

C- ose)

C M

OH

H

OH C=

Basic

# of

carbon

I 1

H

C

OH H

C

OH

Example

H H

Functional

groups

→ All carbs had a

carbonyl

functional

group

Aldose

aldose

can be constitutional Isomers

ketones

Aldose -73 carbon carbs

H

CIO

I 1 I

KO

H

H

I 1 I

H 0

I

C-

H-

OH

1 I

I 1

H