Poly- and heterofunctional compounds

_POLY- AND HETEROFUNCTIONAL COMPOUNDS
Biochemical reactions involve the functional groups of molecules. Alcohols, amines, sulfhydryl groups, aldehydes, ketones, carboxyl groups and esters are all important components of biochemical compounds.
Polyfunctional compounds are the compounds that contain two and more same functional groups.

CH₂  CH  CH₂;
OH OH OH
HOOCCOOH

Heterofunctional compounds are the compounds that contain different functional groups.

• 
  amino-alcohols
  

2 1

CH₂  CH₂
2-aminoethanol

NH₂ OH

• 
  hydroacids
  

• 
  ketoacids
  

O
CH₃  C COOH

• 
  aminoacids
  

H₂N CH₂ COOH

• 
  benzene derivatives
  

2-hydroxopropanoic acid (lactic acid)

pyruvic acid

2-aminoethanoic acid (glycine)

p-aminobenzenesulfonic acid

o-hydroxybenzoic acid

Polyheterofunctional compounds are the compounds that contain more than two different functional groups.

COOH C H  OH CH2COOH	COOH HO  C CH2COOH CH2COOH	COOH HO  C H H  C OH COOH
malic acid	citric acid	tartar acid

This acid performs an important role in biochemical process.

Hydroxyacids
Hydroxyacids are organic compounds that contain a hydroxyl group ( OH ) and
O
a carboxyl group ( C OH ).

The


OH


and


COOH
Chemical properties
groups determines the chemical properties of

hydroxyacids.
Properties of


OH


group.

1. 
   CH₃  CH  COOH  HBr  CH₃  CH  COOH  H₂O OH Br
   
2. 
   CH₃  CH  COOH  2Na  CH₃  CH  COONa  H₂
   

OH ONa

O

3. 
   CH₃ CH COOH + CH₃ C CH₃ CH COOH + HCl
   

Cl

OH O C CH

O

4. 
   The oxidation of hydroxyacids.
   

O H

HO CH₂ C C C OH O OH
Oxidation is carried out in living systems under the control of a dehydrogenase
enzyme such as nicotinamide adenide dinucleotide (NADH).

NAD^
CH  C COOH

CH₃  CH COOH __NA_DH ³
OH _O
lactic acid pyruvic acid Properties of –COOH group.

1. 
   Esterification
   

3 3 3 3
CH  CH  COOH  CH OH ^H CH  CH  COOCH OH OH
ester

2. 
   CH₃  CH  COOH  NaOH  CH₃  CH  COONa  H₂O OH OH
   
3. 
   Formation of amides.
   

CH₃  CH  COOH  NH₃  CH₃  CH  CONH₂  H₂O OH OH

4. 
   Formation of alcohol by decarboxylation.
   

3 3 2 2
CH  CH  COOH ^t0 CH  CH  OH  CO OH
Loss of CO₂ from a molecule is called decarboxylation.

β- hydroxybutyric acid produced by the body. Fatty acids are oxidized to β- hydroxybytyric acid.

β- hydroxybutyric acid is oxidized to acetoacetic acid.

^ 
CH 


NAD^

_ ^ 3 2

3
^{CH CH}2 ^{ COOH CH  C CH  COOH}
NADH,H
OH O
^{CH3  C CH}2 ^{ COOH }_d^_eca^_rbox^_ylat^_ion ^{CH3  C CH3}
CO₂
O O
acetone
Ketone bodies


Ketoacids Ketoacids contains –COOH and –C=O groups.

O

CH₃
^s^ol.H^2SO^{4 ,t}0  CH  C

CO

3
2


H ethanal

C  O

• 
  _c_ons_ent._H₂S_O₄ ,t_⁰ _CH
  

CO

3
2
 COOH ethanoic acid

COOH
_N_AD_H,H_^ <sub>

</sub> 
NAD
CH₃
 CH  COOH
OH lactic acid

O
HOOC  C CH₂COOH oxaloacetic acid O
CH₃  C CH₂COOH acetoacetic (ацетоуксусная)
Amino alcohol contains –NH₂ and –OH groups. HO – CH₂ – CH₂ –NH₂ – 2 – aminoethanol
Amino alcohols are structural components of compound lipids. Amino alcohol reach with acid to poduce salt:
HO  CH  CH  NH  HCl  HO  CH CH NH ^Cl^
2 2 2 2 2 3
2-aminoethanol hydrochloride
2- aminoethanol derivative is medicine.

Димедрол
This is sleeping draught, antiallergy

Choline OH – CH₂ – CH₂ – N⁺(CH₃)₃ is structural components of phosphoglyceride. Preparation of choline:

2 2 2 2 2 2 3 3
HO  CH  CH  COOH ^D^eca^rbo^xyla^tionHO  CH  CH  NH ^m^eth^ylat^ionHO  CH CH N^ (CH )

NH₂
serine
2-amsnoethanol

Chorine reach with CH₃COOh to produse acetylcholine

2 2 3 3 3 2 2 3 3
HO  CH  CH  N^ (CH ) ^C^H3^COO^HCH COOCH  CH N^ (CH )


Chemical properties of o-hydroxybenzoic acid.