BIOLOGICAL METHYLAT

ION
BIOLOGICAL METHYLATION
• The process by which a methyl radical (-CH3) is chemical
ly combined with some other substance through the acti
on of a living organism. One of the most environmentall
y important examples of this process is the methylation
of mercury in the sediments of lakes, rivers, and other b
odies of water. Elementary mercury and many of its inor
ganic compounds have relatively low toxicity because th
ey are insoluble. However, in sediments, bacteria can co
nvert mercury to an organic form, methylmercury, that i
s soluble in fat. When ingested by animals, methylmercu
ry accumulates in body fat and exerts highly toxic, some
times fatal, effects
• Methylation brings about a large difference in such p
hysical properties as boiling point and solubility. Thes
e changes arise primarily from the fact that the meth
yl groups have neither empty orbitals nor non-bondi
ng electrons available for intermolecular interaction.
Methylation also can increase the toxicity of metals
due to the aforementioned changes in physical prop
erties.The increase in volatility and lipophilicity cause
d by methylation brings about the mobility of the me
tals under environmental conditions. Biological meth
ylation of metals can take place both in homogeneou
s aqueous media and in heterogeneous media.
• Example: pb(NO3)2 +CH3I ---------> (CH3)4 pb
• Biomethylating Agents and Mechanism of Methylati
on :
• 1.Methylcobalamin (vitamin B12)
• 2.S-adenosyl methionine and
• 3.Methyl iodide.
Methylcobalamin
• This is one of the coenzyme forms of vitamin B12 fou
nd in bacteria and animals. All corrinoids contain fou
r reduced pyrrole rings, joined into a macrocyclic ring
by four links. Three of the links are formed by the me
thylene =C- groups and the fourth by a C-C bond.The
central cobalt atom is in oxidation state Co(IV). It has
the capacity to coordinate up to six ligands. Of these
coordinate positions, four are occupied by the four n
itrogen atoms of the corrin ring. The fifth position is
occupied by a heterocyclic chain. The sixth is usually
occupied by a methyl group or a water molecule
S-Adenosyl methionine:

• The trimethylarsine was found to carry the label. N

ow we know that the activated form of methionine
is S-adenosylmethionine, which is capable of transf
erring methyl as a carbonium ion. The biomethylati
on of metalloids by S-adenosylmethionine occurs b
y nucleophilic or free radical attack by the metallic s
alt of lower oxidation state
Methyl lodide :

• Both methylcobalamin and methyl iodide have bee

n found to mobilize metals out of water insoluble c
ompounds and/or anoxic sediments. Methylation o
f metals and metalloids in homogeneous aqueous s
olutions has been extensively investigated.Aqueous
solutions of methyl iodide reacted with metal sulfid
es or selenides plus various binary or ternary ores i
nvolving metals combined with sulfur or selenium o
r tellurium.
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