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 bio-
products.
 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 A B
N N N N
O2
Globine Fe Globine Fe
4 N N 4 N N
D C D C

CO 2H CO 2H CO 2H CO 2H

HbO2
Hb
 BIOMIMETIC PRODUCT:
PICKET FENCE PORPHYRINS

H H
H C H
C C
H H

C
H H

N N
Fe
N N

CO 2H CO 2H
 Oxygen will be trapped by the
Porphyrins

H H O2
H C H
C C
H H

C
H H

N N
Fe
N N

CO 2H CO 2H
 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

O Squalene-2,3-epoxide
H+

H
+
H
H

HO
Prosteryl cathion

W-M Rearr.

H
+

HO
LANOSTEROL
 LANOSTEROL BIOSYNTHESIS

O
H+ Squalene-2,3-epoxide

+
H +
H

H
HO
Prosteryl cathion

W-M Rearrng

Lanosterol HO
 Johnson constructed the triene compound to
mimic the natural squalene

Natural Starting material for Johnson's starting material for

construction of Triterpene/Steroid construction of Steroid

CH3
C
C

O OH

Squalene-2,3-epoxide Triene derivative

 Natural Starting material for
construction of Triterpene/Steroid

Enzyme stabilizing
squalene conformation,
both in isoprene terminus
and in the epoxide moeity

Squalene-2,3-epoxide
 Johnson's starting material for
construction of Steroid

Terminus acetylene
moeity will stopn effciently
carbocathion formation

CH3
C
C

OH
The cyclopentanoid
moeity used to stabilize
the triene conformation
Triene derivative
 Johnson’s Biomimetic Synthesis of
Progesteron
CH3
C O
C HOCH2CH2OH
ClCH2CH2Cl
CF 3COOH H

0oC H H

OH

1). MeOH, O 3, -70 oC

2). Aq. AcOH, Zn
3). Aq. KOH, 20hr

H H
O

Progesteron
 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