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BIOMIMETICS
Biomimetics is the scientific method of learning new principles and processes based on systematic
study, observation and experimentation with live animals and organisms.
Biomimetics is a novel approach to developing designs and products or to solving human problems
by taking inspiration from nature.
Biomimetics at the molecular level:
Imitating and learning from nature, based on our understanding of molecular biology and
biochemistry will enable innovation and develop designs to solve human problems.
THE BIOMOLECULES
CARBOHYDRATES
Carbohydrates are the most abundant biological molecule and most of them consist of carbon, hydrogen
and oxygen in a 1:2:1 ratio (CH2O)n. Carbohydrates contain either an aldehyde moiety or a ketone moiety
with large quantities of hydroxyl groups. The presence of the hydroxyl groups allows carbohydrates to
interact with the aqueous environment and to participate in hydrogen bonding, both within and between
chains.
n Category
3 Triose
4 Tetrose
5 Pentose
6 Hexose
ISOMERISM in Carbohydrates
Stereoisomerism
H H
Enantiomers two molecules that are mirror-images to each
H OH H OH other and cannot be superimposed on each other
H OH HO H
D dextrorotatory, (+) clockwise rotation, position of hydroxyl
H OH H OH group on the reference carbon is on the right of the projection
H H formula
D-glyceraldehyde L-glyceraldehyde
L levorotatory, (-) counterclockwise rotation, position of the
* D-form monosaccharides are hydroxyl group on the reference carbon is on the left of the
used to construct carbohydrates. projection formula
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Mapua Institute of Technology Introduction to Biomimetics Engineering and Biocomponent Design
School of Chemical Engineering and Chemistry THE BIOMOLECULES
D-glucose
H OH H OH
Sucrose: prevalent in sugar cane and sugar beets, is composed of glucose and fructose through an -
(1,2)-glycosidic bond.
Lactose: is found exclusively in the milk of mammals and consists of galactose and glucose in a -(1,4)
glycosidic bond.
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Mapua Institute of Technology Introduction to Biomimetics Engineering and Biocomponent Design
School of Chemical Engineering and Chemistry THE BIOMOLECULES
Maltose: the major degradation product of starch, is composed of 2 glucose monomers in an -(1,4)
glycosidic bond.
To describe disaccharides or oligosaccharides, the end of a chain that has a free anomeric carbon is
called the reducing end.
HOMOPOLYSACCHARIDES
Storage Polysaccharides
a. Starch is the major form of stored carbohydrate in plant cells. It is actually a mixture of two
compounds, amylose (unbranched with glucose units linked (14) and amylopectin ( (14) links
with (16) links approximately every 25-30 glucose residues). Unbranched starch is called amylose;
branched starch is called amylopectin.
The unbranched structure of amylose causes the polymer to exist as a long, coiled helix under
conditions when it can be stabilized. One substance that will stabilize an amylose helix is iodine, which
fits into the hollow core of the structure. Binding of iodine to amylose helices produces an intense blue
color and has long been used as a qualitative test for starch. Polymers consisting solely of glucose are
called glucans.
Amylopectin is a polymer of glucose. It differs from amylose and resembles the animal storage
polysaccharide, glycogen, in containing (16) branches in addition to (14) links between glucose
units.
b. Glycogen is a branched polymer of glucose, consisting of main branches of glucose units joined in
(14) linkages. Every 7-20 residues, (16) branches of glucose units are also present. It is the
primary energy storage material in muscle. Individual glucose units are cleaved from glycogen in a
phosphorolytic mechanism catalyzed by glycogen phosphorylase.
Glycogen is a very compact structure that results from the coiling of the polymer chains. This
compactness allows large amounts of carbon energy to be stored in a small volume, with little effect on
cellular osmolarity.
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Mapua Institute of Technology Introduction to Biomimetics Engineering and Biocomponent Design
School of Chemical Engineering and Chemistry THE BIOMOLECULES
Structural Polysaccharides
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Mapua Institute of Technology Introduction to Biomimetics Engineering and Biocomponent Design
School of Chemical Engineering and Chemistry THE BIOMOLECULES
LIPIDS
- provide energy reserves, predominantly in the form of triacylglycerols.
- serve as structural components of biological membranes.
- both lipids and lipid derivatives serve as vitamins and hormones.
STORAGE LIPIDS
a. FATTY ACIDS
Solubility to water
- FAs have poor solubility in H2O
*the longer the FA chain and fewer double bonds, the lower its solubility in water.
Ex: Arrange the ff. FAs accdg. to increasing solubility in water: 16:0; 20:0; 18:0; 16:1
9
Melting point
- unsaturated FAs have lower MP than saturated FAs.
% Fatty Acid
State at RT Saturated Unsaturated
25C C4-C12 C14 C16 C18 C16 + C18
Olive oil Liquid <2 <2 13 3 80
Butter Solid (soft) 11 10 26 11 40
Beef fat Solid (hard) <2 <2 29 21 46
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Mapua Institute of Technology Introduction to Biomimetics Engineering and Biocomponent Design
School of Chemical Engineering and Chemistry THE BIOMOLECULES
Triacylglycerols simplest lipids constructed from FAs which functions as energy storage and
insulation. TAG or fats are in form of solids and oil. Fats which are rich in unsaturated fatty acids are
typically oils. When lipid-rich foods are exposed too long to air, they become rancid as a result from the
oxidative cleavage of their double bonds in the chain.
TAGs yield 2x as much energy as CHOs (stored in adipocytes or fat cells; seeds in plants)
TAGs provide insulation: seals, walrus, penguins
TAGs have low density: in sperm whales, TAGs allows the animal to match the buoyancy of their
bodies to that of their surroundings.
Hydrolysis of TAGs produces soaps by heating them with NaOH or KOH. This process is called
+ +
saponification which produces glycerol and Na or K salts of the fatty acids known as the soap.
O O
+
H2C O C R1 H2C OH K -O C R1
O 3KOH O
+
HC O C R2 HC OH K -O C R2
O O
+
H2C O C R3 H2C OH K -O C R3
STRUCTURAL LIPIDS
Phospholipids
are a class of lipids that are a major component of all cell membranes or plasma membrane as they can
form lipid bilayers.
The cell membrane lipid bilayer is semi-permeable. It only allow small nonpolar molecules such as CO2
and O2 to pass through the membrane. Other molecules need a transporter in order to move across the
membrane.
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Mapua Institute of Technology Introduction to Biomimetics Engineering and Biocomponent Design
School of Chemical Engineering and Chemistry THE BIOMOLECULES
The cell membrane consists of two layers of phospholipids that arranged in a fashion by which the
nonpolar portions are sandwiched in between the polar portions. The lipid bilayer also consists of other
biomolecules such as peripheral protein and integral proteins that aid in transport of molecules;
carbohydrates for cell recognition; and cholesterol.
Chitosan has been used in many medical applications. It serves as biomimetic material of anti-
hemoglobin antibodies to create an imprinted recognition surface of hemoglobin beads.
Welan gum that exhibits high rheological property is used as admixtures for eco-efficient
construction materials e.g. concretes.
Biomimetic membranes may provide an alternative to current reverse osmosis and nanofiltration
membranes e.g. for industrial separation and wastewater treatment.
In the creation of biosensors, a lipid layer that mimics the cell membrane served as an
impermeable barrier around the wire where a membrane protein (bio-element) can be
incorporated.
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Mapua Institute of Technology Introduction to Biomimetics Engineering and Biocomponent Design
School of Chemical Engineering and Chemistry THE BIOMOLECULES
AMINO ACIDS
Amino acids are the building blocks of proteins. An amino acid consists of an asymmetric carbon (-
carbon) at the center with four different groups attached to it: an amino group, a carboxyl group, a
hydrogen atom and a variable group, R (except for glycine). Thus amino acids have chiral centers.
Peptides are named from sequence of their constituent amino acids, beginning from the amino terminal
residue at the left proceeding toward the carboxyl terminus at the right.
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Mapua Institute of Technology Introduction to Biomimetics Engineering and Biocomponent Design
School of Chemical Engineering and Chemistry THE BIOMOLECULES
PROTEIN
Proteins are biopolymers (called polypeptides) of L-amino acids.
Only L-amino acids are used to make proteins (rare exceptions of proteins in bacterial cell wall, which
contain some D-amino acids)
The process of putting amino acids together to make proteins is called translation. Translation relies on
the genetic code, in which three nucleotides in mRNA specify one amino acid in protein.
The difference between a polypeptide and a protein is that the term polypeptide refers simply to a chain of
amino acids. The term protein refers to the chain of amino acids after it folds properly and is (in some
cases) modified. Proteins may consist of more than one polypeptide chain.
Proteins are sometimes described as the "workhorses" of the cell because they do so many things -
catalyze reactions, provide structural integrity, transport molecules, provide movement, bind molecules,
and others.
Function of Proteins
a. Transport e. Defense
b. Nutrient and storage f. Regulation of cellular or physiological activity
c. Contraction g. Catalyst
d. Structure or support
Protein Structure
The order or sequence of amino acids distinguishes different proteins from each other. The sequence of
amino acids determines the 3-dimensional shape of the protein. Alterations to the amino acid sequence of
a protein changes its 3D shape.
Primary structure is the most basic level of protein structure. It is the linear sequence of amino acids.
The primary structure of a protein is specified by the order of bases in the genomic DNA. Different
sequences of the acids along a chain, however, affect the structure of a protein molecule in different
ways.
Secondary structures are stable and occur widely in proteins (globular and fibrous). Most prominent are
the -helix and -conformation. The simplest arrangement the polypeptide chain could assume with its
rigid peptide bonds is a helical structure that is right-handed.
-Helical structure (right-handed) is predominant in -
keratin. Secondary structures are stabilized by favorable
hydrogen bonding between residues and have been brought
into close juxtaposition by folding or coiling of the primary
structure. In the -conformation, the backbone of the
polypeptide chain is extended into a zigzag manner (-
pleated sheets) and the hydrogen bonding can either be
intrachain or interchain between peptide linkages of adjacent
polypeptide chains.
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Mapua Institute of Technology Introduction to Biomimetics Engineering and Biocomponent Design
School of Chemical Engineering and Chemistry THE BIOMOLECULES
ENZYMES
- Most enzymes are proteins.
- They function as catalyst in biological reactions.
- Enzymes are globular proteins - their molecules are round
in shape.
- Each enzyme has a specific catalytic action.
- Their normal activity depends on their environment.
- Abnormal conditions cause reduced activity
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Mapua Institute of Technology Introduction to Biomimetics Engineering and Biocomponent Design
School of Chemical Engineering and Chemistry THE BIOMOLECULES
NUCLEIC ACIDS
Nucleic acids are complex structures composed of nucleotide chains that are used to maintain genetic
information.
CH3 N N
N HN HN HN HN
O N O N O N N N H2N N N
H H H H H
CYTOSINE (C) URACIL (U) THYMINE (T) ADENINE (A) GUANINE (G)
NH2 O NH2
O O
CH3 N
N HN N C N
HN HN C
CH
CH
HC C
N O N O N C C
O N N N
H2N N
HO HO HO
O O HO HO
O O O
OH OH OH OH OH OH OH OH OH OH
CYTIDINE URIDINE THYMIDINE ADENOSINE GUANOSINE
C
P U T A G
O P P P P
O O O O
OH OH
OH OH OH OH OH OH OH OH
Cytidine Uridine Thymidine Adenosine Guanosine
monophosphate monophosphate monophosphate monophosphate monophosphate
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Mapua Institute of Technology Introduction to Biomimetics Engineering and Biocomponent Design
School of Chemical Engineering and Chemistry THE BIOMOLECULES
Nucleic acids are formed through linkage of one nucleotide with another by forming a covalent
bond called 3,5-phosphodiester bond. The next nucleotide to be attached to the growing
polynucleotide chain is always added at the 3-end.
Nucleic acids are constructed starting from the 5-end going to the 3-end
Example: 5- ATG CCC GGG AAA GCG TTT CCG.-3
The DNA molecule consists of 2 strands of polynucleotide held together through hydrogen bonding
interaction of the bases contained in the 2 strands. This pairing of bases is called complimentary base
pairs: A=T and CG
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Mapua Institute of Technology Introduction to Biomimetics Engineering and Biocomponent Design
School of Chemical Engineering and Chemistry THE BIOMOLECULES
DNA-inspired: World's first curved double helix bridge at Marina Bay, Singapore
Bridge measures 280 meters long made of a special stainless steel. If all the steel tubes forming the major
and minor helix are laid end to end, it will measure 2,250 meters long, and the entire structure weighs about
1,700 tons, which is equivalent to about 1,130 saloon cars.
References:
Yosef Bar Cohen, Biomimetics Biologically Inspired Technologies, CRC press, 2006.
Hyun Ok Ham, et al., J. Am. Chem. Soc., 2013, 135 (35), pp 1301513022.
Varinder Kaur, Manav B. Bera, Parmjit S. Panesar, Harish Kumar, J.F. Kenned, Int. Journ. of Biological
Macromolecule, 2014
M. Lasheras-Zubiate, I. Navarro-Blasco, J. M. Fernndez and J. I. Alvarez, Journal of Applied Polymer
Science, 2010.
Torben Lenau, Biomimetics as a Design Methodology, Intl Conf. on Engg Des. Stanford Univ., 2009
nd
Voet and Voet, Biochemistry 2 ed. Wiley Publication (2004).
rd
Voet, Voet and Pratt, Biochemistry 3 edition (2008), Wiley and Sons.
th
Starr and Taggart (2004). Biology. The Unity and Diversity of Life, 10 edition, Wadsworth Group,
Thomson Learning, Inc., California
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