BIOMIMETICS CHEMISTRY
New Field in Chemistry
Emerging from the Advancement of Biotechnology
Workshop on
The Establishment of BINASIA Indonesia Nodal
27-28 July 2005, Jakarta, Indonesia
UMAR A. JENIE
Indonesian Institute of Sciences (LIPI);
Department of Medicinal Chemistry,
Faculty of Pharmacy, Gadjah Mada University (UGM)
BIOMIMETICS CHEMISTRY

Biomimetics chemistry is not Biotechnolgy, it is a new
field in Chemical Sciences concerns with synthesizing
product/s that could imitate (mimics) biological function
and processes.

Development of biomimetics chemistry depends mainly
in the advancement of molecular based biotechnology
which elucidating biosynthetic mechanism of bioproducts.
Molecular Biology
Mechanisms of Biological activities and
Biosynthesis mechanisms
Biomimetic Chemistry
Biomimetic Products & Processes
BIOMIMETICS CHEMISTRY is a branch of
chemistry that study on how to make products:

Biomimetic Products (making products having
function similar or identical to that of the
biological products)

Biomimetic Processes (organic synthesis based
on biosynthetic mechanisms)
BIOMIMETIC PRODUCTS

ARTIFICIAL BIOPRODUCTS
Example: Artificial Hb
Organic chemists have been trying to construct and
develop organic molecule that have capability to cacth
up reversibly oxygen from the air, similar to that of the
haemoglobine.
This molecule called:
PICKET FENCE PORPHYRINS.
Haem binds oxygen reversibly
O O
A
B
N
N
O2
Fe
Globine
4
N
N
D
C
CO 2H
CO 2H
Hb
A
B
N
Globine
4
N
Fe
N
N
D
CO 2H
C
CO 2H
HbO2
BIOMIMETIC PRODUCT:
PICKET FENCE PORPHYRINS
H
H
H
C
C
C
H
H
C
H
N
N
Fe
N
C O 2H
N
C O 2H
H
H
Oxygen will be trapped by the
Porphyrins
H
H
C
C
C
H
H
C
H
N
N
Fe
N
CO 2H
O2
H
N
CO 2H
H
H
BIOMIMETIC PROCESS

BIOSYNTHESIS PATHWAY
Organic chemists have been inspired by biosynthesis
pathways of secondary metabolites occurred in nature.
They are using such natural mechanism to construct
natural products. Such approach known as Biomimetic
Synthesis.
BIOMIMETIC PROCESS
based on Biosynthetic Mechanism

LANOSTEROL BIOSYNTHESIS
lanosterol biosynthesis proceeds via Mevalonic Pathway,
in which the intermediate squalene-2,3-epoxide
undergoes protonation, followed by MW rearrangement
to produce lanosterol.
LANOSTEROL BIOSYNTHESIS
H+
O
Sq uale ne -2, 3-e p o xid e
H
+
H
H
HO
Pro s te ryl c athio n
W-M Re arr.
+
HO
LANO STERO L
H
LANOSTEROL BIOSYNTHESIS
O
H+
Squalene-2, 3-epoxide
H
+
+
H
H
HO
P rost eryl cat hion
W-M R earrng
Lanosterol
HO
Johnson constructed the triene compound to
mimic the natural squalene
Natural Starting material for
construction of Triterpene/ Steroid
Johnson' s starting material for
construction of Steroid
CH3
C
C
O
OH
Squalene-2,3-epoxide
Triene derivative
Natural Starting material for
construction of Triterpene/Steroid
Enz yme s tab iliz ing
s q uale ne c o nfo rmatio n,
b o th in is o p re ne te rminus
and in the e p o xid e mo e ity
O
Squalene-2,3-epoxide
Johnson's starting material for
construction of Steroid
Terminus ac etylene
moeity will s topn effc iently
c arboc athion formation
CH3
C
C
OH
The c yc lopentanoid
moeity us ed to s tabilize
the triene c onformation
Triene derivative
Johnson’s Biomimetic Synthesis of
Progesteron
CH3
C
C
O
HO CH2CH2O H
ClCH2CH2Cl
CF3CO O H
H
0oC
H
OH
1). Me O H, O
3, -70oC
2). Aq . Ac O H, Z n
3). Aq . KO H, 20hr
O
H
H
H
O
P rogesteron
H
FUTURE DEVELOPMENT

Biomimetic techniques could be used for
synthesis of a complex biological molecules,
such as steroids, with shorter step of reactions
than the conventional ones.

Biomimetic techniques could also overcome
stereochemical problems faced by conventional
synthesis
THANK YOU