Analytical Chemistry

College of Allied Health Sciences

Bachelor of Science in Medical Laboratory Science
Second Semester, A.Y. 2022-2023

[TRANS] BIOCHEM SUMMARY

o Hydroxyl groups replaced by hydrogens, e.g., 2-
OUTLINE deoxy-D-ribose in DNA.
 Sugar Esters:
I Carbs o Phosphate esters, important in metabolic pathways
II Lipids and nucleotide structure.

AMINO SUGARS:
CARBOHYDRATES:  Definition: Amino sugars, such as D-glucosamine and D-
 Abundant organic molecules in nature, derived from galactosamine, have an amino group at the C-2 position
sunlight through photosynthesis. Metabolic precursors of instead of a hydroxyl group.
biomolecules, vital for energy in animals, and play structural  Occurrence: Found in oligosaccharides and
roles in cells. polysaccharides, including chitin in crustaceans and
insects.
CLASSIFICATION:
 Monosaccharides: ACETALS, KETALS, AND GLYCOSIDES:
o Simple sugars (CH2O)n, cannot be broken down  Reaction:
under mild conditions. o Hemiacetals and hemiketals can react with alcohols
 Oligosaccharides: to form acetals and ketals, leading to the formation
o Few sugar residues (2-10), often covalently linked to of glycosides.
other molecules.  Glycosidic Bond:
 Polysaccharides: o The new bond between the anomeric carbon atom
o Polymer of simple sugars, linear or branched, with and the oxygen atom of the alcohol is called a
high molecular weights. glycosidic bond.

MONOSACCHARIDE CLASSIFICATION: OLIGOSACCHARIDES:

 Aldoses vs. Ketoses:  Composition:
o Based on the presence of aldehyde or ketone group. o Formed from a relatively small number of different
 Stereochemistry: monosaccharide units.
o Chiral centers, designated as D or L based on  Monosaccharide Units:
configuration compared to glyceraldehyde. o Include hexoses (glucose, fructose, mannose,
galactose) and pentoses (ribose, xylose).
MONOSACCHARIDE FORMS:  Disaccharides:
 Cyclic Forms: o The simplest oligosaccharides, consisting of two
o Can form pyranose or furanose rings through monosaccharide units linked by a glycosidic bond.
intramolecular reactions.
 Anomers: DISACCHARIDES:
o Isomers differing in configuration at the anomeric  Sucrose:
carbon; o Composed of fructose and glucose, nonreducing
 Haworth Projections: sugar.
o Represent cyclic structures, showing substituents  Maltose:
above or below the ring. o Composed of two glucose units linked in a -
configuration.
STEREOISOMERS:  Cellobiose:
 Enantiomers: Mirror images. o 1⎯→4 linked glucose units in a -configuration.
 Diastereomers: Not mirror images.  Isomaltose:
 Epimers: Diastereomers differing in configuration at one o Glucose units linked in a -configuration.
chiral center.  Lactose:
o Principal carbohydrate in milk, composed of D-
CONFORMATIONS OF RINGS: galactose and D-glucose with a (1⎯→4) link.
 Chair and Boat Conformations:
o Pyranose rings exhibit puckered conformations. POLYSACCHARIDES:
 Substituent Orientation:  Definition:
o Equatorial preferred for stability. o Glycans composed of monosaccharides and their
derivatives.
DERIVATIVES OF MONOSACCHARIDES:  Homopolysaccharide:
 Sugar Acids: o Contains only one kind of monosaccharide molecule.
o Result from oxidation, reducing sugars involved in  Heteropolysaccharide:
chemical tests. o Contains more than one kind of monosaccharide.
 Sugar Alcohols (Alditols):  Common Constituents:
o Result from reduction, sweet-tasting; sorbitol, o D-glucose, D-fructose, D-galactose, L-galactose, D-
mannitol, and xylitol. mannose, L-arabinose, D-xylose, amino sugars, and
 Deoxy Sugars: sugar acids.
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 Functions:
o Serve as energy storage (starch, glycogen),
structural support (chitin, cellulose), or protective
substances (mucopolysaccharides).
 Branching:
o Polysaccharides can form branched structures,
distinguishing them from linear polymers like
proteins and nucleic acids.
 Advanced Functions:
o Recent research indicates involvement in cellular
recognition and intercellular communication.
SUMMARY:
 Polysaccharides are used by organisms for energy storage
and structural support.
STARCH:
 Most common storage polysaccharide in plants.
 Composed of amylose (linear chains of D-glucose) and
amylopectin (branched chain).
 Starch granules in plant cells, split into monosaccharides by
starch phosphorylase during mobilization.
GLYCOGEN:
 Main storage polysaccharide in animals, found in liver and
muscle.
 Highly branched molecules with (1⎯→6) branches.
 Hydrolyzed by amylases, and glycogen phosphorylase.
DEXTRANS:
 (1⎯→6)-linked polysaccharides of D-glucose with branched
chains.
 Found in yeast and bacteria, important in dental plaque
formation.
CELLULOSE:
 Structural polysaccharide in plant cell walls.
 Linear homopolymer of D-glucose units linked by (1⎯→4)-
glycosidic bonds.
 Forms extended ribbons with strong hydrogen bonding.
 Resistant to hydrolysis in most animals except ruminants,
termites, and shipworms.
CHITIN:
 Similar to cellulose, found in fungi cell walls and
exoskeletons of crustaceans, insects, and spiders.
 N-acetyl-D-glucosamines in (1⎯→4) linkage.
 Forms extended ribbons, can occur in parallel or antiparallel
arrangements.
AGAROSE:
 Polysaccharide mixture isolated from marine red algae.
 Consists of agarose and agaropectin.
 Agarose forms a double helix with a threefold screw axis
and can form gels with high water content.
GLYCOSAMINOGLYCANS:
 Linear chains of repeating disaccharides with amino sugar
and negatively charged groups.
 Examples include heparin, hyaluronate, chondroitins,
keratan sulfate, and dermatan sulfate.
 Found in extracellular matrix, vitreous humor, synovial fluid,
tendons, cartilage, and skin.
PEPTIDOGLYCAN:
 Polysaccharide of bacterial cell walls, providing strength
and rigidity.
 Gram-positive bacteria have thick cell walls, Gram-negative
bacteria have thinner walls.
 Consists of a backbone with N-acetylglucosamine and N-
acetylmuramic acid units.
 Crosslinked with tetrapeptide and pentaglycine chain in
Gram-positive bacteria.
GLYCOPROTEINS:
 Proteins with covalently linked oligosaccharide and
polysaccharide groups.
 Can be O-linked (to serine, threonine, or hydroxylysine) or
N-linked (to asparagine).
 Found in various cellular functions, including structural
proteins, enzymes, membrane receptors, transport
proteins, and immunoglobulins.
CELL SURFACE POLYSACCHARIDES IN ANIMALS:
 Animal cells display diverse glycoproteins on the cell
surface for communication.
 Important in cell recognition and interactions.
 Examples include leukosialin, mucins, LDL receptor, and
decay-accelerating factor (DAF).
GALECTINS:
 Family of conserved proteins with carbohydrate recognition
domains (CRDs) of about 135 amino acids.
 Bind specifically to galactosides.
 Present in both vertebrates and invertebrates, involved in
cell adhesion, growth regulation, inflammation, immunity,
and cancer metastasis.
 Human galectins associated with increased risk of heart
attacks and implicated in inflammatory bowel disease.
 Structure of human galectin-1 is a dimer of antiparallel beta-
sandwich subunits; lactose binds at opposite ends of the
dimer.
 Amino acid residues involved in galactose binding are
maintained in the absence of ligand by a hydrogen-bonded
network of four water molecules.
C-REACTIVE PROTEIN (PENTRAXIN):
 Pentraxins are lectins with an unusual quaternary structure,
forming a planar ring with a central hole.
 C-reactive protein (CRP) is a pentraxin that limits tissue
damage, acute inflammation, and autoimmune reactions.
 Functions by binding to phosphocholine moieties on
damaged membranes.
 Binding of CRP to phosphocholine is mediated through a
bound calcium ion and a hydrophobic interaction.
 CRP acts to limit inflammation damage and is involved in
immune responses.
LIPIDS IN BIOLOGICAL SYSTEMS:
 Lipids in biological systems can be hydrophobic (nonpolar
groups only) or amphipathic (both polar and nonpolar
groups).
 Hydrophobic nature of lipid molecules enables membranes
to act as effective barriers to polar molecules.
 This chapter discusses the chemical and physical
properties of various lipid molecules, while the next chapter
explores membranes, which depend on lipid constituents.
FATTY ACIDS (CHAPTER 8.1):
 Fatty acids consist of a long hydrocarbon chain ("tail") and
a terminal carboxyl group ("head").
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 Typically esterified to glycerol or other backbone structures
in biological systems.
 Most fatty acids in nature have an even number of carbon
atoms (usually 14 to 24).
 Can be saturated (all single bonds) or unsaturated (one or
more double bonds).
 Monounsaturated if one double bond, polyunsaturated if
more than one.
 Essential fatty acids like linoleic and -linolenic acids, not
synthesized by mammals, must be obtained from the diet.
 Saturated fatty acids are flexible due to free rotation around
carbon–carbon bonds; unsaturated fatty acids have a bend
or "kink" due to cis configuration.
 Diets high in saturated fatty acids are correlated with
cardiovascular disease, while those higher in unsaturated
fatty acids may reduce the risk.
CANOLA OIL (SPECIFIC EXAMPLE):
 Canola oil, derived from rapeseed, is promoted as a healthy
dietary oil.
 Composed primarily of oleic acid, linoleic acid, and α-
linolenic acid with low saturated fat content.
 Conventional breeding reduced erucic acid content, making
it suitable for consumption.
 Diets high in trans fatty acids, formed by bacterial reactions
or partial hydrogenation, contribute to cardiovascular
disease.
 Canola oil is an example of an oil with beneficial fatty acid
composition.
TRIACYLGLYCEROLS (CHAPTER 8.2):
 Triacylglycerols, or triglycerides, are a major energy
reserve in plants and animals.
 Composed of glycerol esterified with three fatty acids.
 Simple triacylglycerols have identical fatty acid groups;
mixed triacylglycerols have different ones.
 Hydrolysis of triacylglycerols results in salts of free fatty
acids and glycerol (saponification).
 Triacylglycerols are hydrophobic, aggregate in anhydrous
forms, and provide a rich source of energy.
GLYCEROPHOSPHOLIPIDS (CHAPTER 8.3):
 Glycerophospholipids, also known as phosphoglycerides,
are essential components of cell membranes.
 Consist of a 1,2-diacylglycerol with a phosphate group
esterified at carbon atom 3 of the glycerol backbone.
 One of the largest and most important classes of natural
lipids.
 Found in cell membranes and in small concentrations in
other parts of the cell.
GLYCEROPHOSPHOLIPIDS (PHOSPHOLIPIDS):
 Glycerophospholipids, also known as phosphoglycerides,
are a major class of natural lipids.
 They are essential components of cell membranes and are
found in small concentrations in other parts of the cell.
 Glycerophospholipids have a phosphate group esterified at
carbon atom 3 of the glycerol backbone.
 The stereospecific numbering or sn-system is used for
naming glycerophospholipids based on prochirality.
 Common head groups in phosphatides include choline,
ethanolamine, glycerol, serine, and inositol.
ETHER GLYCEROPHOSPHOLIPIDS:
 Ether glycerophospholipids, such as platelet-activating
factor (PAF) and plasmalogens, have an ether linkage at
the C-1 position of glycerol.
 PAF functions as a soluble messenger in signal
transduction.
 Plasmalogens have a cis-unsaturated alkyl moiety.
SPHINGOLIPIDS:
 Sphingolipids are a class of lipids with sphingosine as the
backbone.
 Ceramides, sphingomyelins, cerebrosides, and
gangliosides are examples of sphingolipids.
 Glycosphingolipids, including cerebrosides and
gangliosides, play roles in cell recognition and tissue
specificity.
 Genetic diseases may involve the accumulation of specific
glycosphingolipids.
WAXES:
 Waxes are esters of long-chain alcohols with long-chain
fatty acids.
 They are water-insoluble and provide water-repellant
characteristics to various surfaces.
 Examples include carnauba wax and lanolin.
TERPENES:
 Terpenes are lipids formed from combinations of isoprene
units.
 Monoterpenes, sesquiterpenes, diterpenes, triterpenes,
and tetraterpenes are examples of terpenes.
 Terpenes play roles in various biological processes, and
some are precursors to important molecules like
cholesterol.
STEROIDS:
 Cholesterol is a common steroid in animals and a principal
component of cell membranes.
 Steroid hormones, including androgens, estrogens,
progestins, glucocorticoids, and mineralocorticoids, are
derived from cholesterol.
 Steroids have diverse roles in cellular functions, including
the regulation of metabolism and reproduction.
LIPID METABOLISM AND SIGNALING:
 Lipid metabolism involves the breakdown and modification
of glycerophospholipids and sphingolipids.
 Enzymes like phospholipases play a role in releasing fatty
acids and generating lipid signal molecules.
 Eicosanoids, produced from arachidonic acid, act as local
hormones in response to injury and inflammation.
 Sphingosine-1-phosphate (S1P) is a sphingolipid-derived
signal molecule with various cellular effects.
LIPIDOMICS:
 Lipidomics is an emerging field that involves the global
analysis of lipids and their interacting protein partners.
 Lipidomics can provide insights into cell, tissue, and organ
physiology, offering a comprehensive understanding of lipid
function in health and disease.
SUMMARY
Overall, lipids play critical roles in cellular structure, function, and
signaling, and advancements in lipidomics contribute to a
deeper understanding of their involvement in various
physiological processes.
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