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Biochemistry Lecture Notes: Carbohydrates and Their Stereochemistry, Study notes of Biochemistry

An in-depth exploration of carbohydrates, their role in providing energy, their structures, and the stereochemistry of chiral carbons. Topics include monosaccharides, disaccharides, and polysaccharides, as well as their classification, properties, and reactions. The document also covers the concept of chiral carbons, enantiomers, and the 2 raised to n rule.

Typology: Study notes

2022/2023

Available from 03/28/2024

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BIOCHEMISTRY TRANSES
Lecture/First Semester
CARBOHYDRATES
Carbohydrates
-provide energy through oxidation
- serve as a form of stored chemical energy
-supply carbon for the synthesis of cell components
- form part of the structures of some cells and tissues
- a molecule that contains the elements CHO in a 1:2:1
ratio
- sizes vary (simple and complex carbohydrates)
- building block is simple sugar or monosaccharide
- Carbohydrates or saccharides (saccharon) are
polyhydroxy aldehydes or ketones, or substances that
yield such compounds on hydrolysis
- An aldehyde is an organic compound in which
the carbonyl group is attached to a carbon
atom at the end of a carbon chain. A ketone is
an organic compound in which the carbonyl
group is attached to a carbon atom within the
carbon chain.
Stereochemistry of Carbohydrates
- Two Forms of Glyceraldehyde (enantiomers)—not
the same as each other; one enantiomer cannot be
superimposed on the other. Enantiomers are mirror
images of each other.
-D-glyceraldehyde
-L-glyceraldchyde
Chiral Carbons
- any carbon atom which is connected to four different
groups will be CHIRAL, and will have two
nonsuperimposable mirror images (The mirror images
are called enantiomers)
- An achiral object is identical with (superimposable on)
its mirror image.
2 raised to n Rule
- when a molecule has more than one chiral carbon,
each carbon can possibly be arranged in either the
right-hand or left-hand form, thus if there are n chiral
carbons, there are 2n possible stereoisomers
Fischer Projection
- are a convenient way to represent mirror images in two
dimensions
- Place the carbonyl group at or near the top and the last
achiral carbon at the bottom
Naming Stereoisomers
- look at the chiral carbon farthest from the carbonyl
group:
- if the hydroxyl group points to right when the
carbonyl is up, it is the D-isomer
- if the hydroxyl group points to left when the
carbonyl is up, it is the L-isomer
Chiral Carbon Atoms
Classes of Carbohydrates
A. Monosaccharides
- simplest of the carbohydrates,since they
contain only one polyhydroxy aldehyde or
ketone
- Monosaccharides are classified according to
the number of carbon atoms they contain:
- 3 carbon atoms - triose
- 4 carbon atoms - tetrose
- 5 carbon atoms - pentose
- 6 carbon atoms - hexose
- The presence of an aldehyde is indicated by
the prefix aldo- and an ketone by the prefix
keto-
- Properties of Monosaccharides
(Carbohydrates)
- monosaccharides & disaccharides
are white crystalline substance;
starches are amorphous powder;
cellulose is fibrous
- solubility to ordinary solvents is
inversely proportional to the
complexity of their structures
- monosaccharides & disaccharides
are sweet; starch and cellulose are
tasteless
-Reducing power - the potential or
power of any substance to reduce
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Lecture/First Semester

CARBOHYDRATES

Carbohydrates

  • provide energy through oxidation
  • serve as a form of stored chemical energy
  • supply carbon for the synthesis of cell components
  • form part of the structures of some cells and tissues
  • a molecule that contains the elements CHO in a 1:2: ratio
  • sizes vary (simple and complex carbohydrates)
  • building block is simple sugar or monosaccharide
  • Carbohydrates or saccharides (saccharon) are polyhydroxy aldehydes or ketones , or substances that yield such compounds on hydrolysis - An aldehyde is an organic compound in which the carbonyl group is attached to a carbon atom at the end of a carbon chain. A ketone is an organic compound in which the carbonyl group is attached to a carbon atom within the carbon chain. **Stereochemistry of Carbohydrates
  • Two Forms of Glyceraldehyde (** enantiomers )— not the same as each other; one enantiomer cannot be superimposed on the other. Enantiomers are mirror images of each other.
  • D-glyceraldehyde
  • L-glyceraldchyde Chiral Carbons
  • any carbon atom which is connected to four different groups will be CHIRAL, and will have two nonsuperimposable mirror images (The mirror images are called enantiomers)
  • An achiral object is identical with (superimposable on) its mirror image. 2 raised to n Rule
  • when a molecule has more than one chiral carbon, each carbon can possibly be arranged in either the right-hand or left-hand form, thus if there are n chiral carbons, there are 2n possible stereoisomers Fischer Projection
  • are a convenient way to represent mirror images in two dimensions
  • Place the carbonyl group at or near the top and the last achiral carbon at the bottom Naming Stereoisomers
  • look at the chiral carbon farthest from the carbonyl group:
  • if the hydroxyl group points to right when the carbonyl is up, it is the D-isomer
  • if the hydroxyl group points to left when the carbonyl is up, it is the L-isomer Chiral Carbon Atoms Classes of Carbohydrates A. Monosaccharides
  • simplest of the carbohydrates,since they contain only one polyhydroxy aldehyde or ketone
  • Monosaccharides are classified according to the number of carbon atoms they contain:
  • 3 carbon atoms - triose
  • 4 carbon atoms - tetrose
  • 5 carbon atoms - pentose
  • 6 carbon atoms - hexose
  • The presence of an aldehyde is indicated by the prefix aldo- and an ketone by the prefix keto- - Properties of Monosaccharides (Carbohydrates)
  • monosaccharides & disaccharides are white crystalline substance; starches are amorphous powder; cellulose is fibrous
  • solubility to ordinary solvents is inversely proportional to the complexity of their structures
  • monosaccharides & disaccharides are sweet; starch and cellulose are tasteless
  • Reducing power - the potential or power of any substance to reduce

Lecture/First Semester another substance. Substance is able to donate electrons.

  • Fermentation - Sugar undergoing fermentation (with yeast) produces ethyl alcohol and carbon dioxide
  • Osazone formation - The reaction (oxidation) between three moles of phenylhydrazine and one mole of aldose produces a crystalline product known as phenylosazone
  • Action of alkalis - Strong alkalies, like strong acids, decompose the sugars. This process identifies the reducing property of sugar
  • Action of acids - acid-catalyzed aldolized glycosides hydrolyzed back to alcohol & sugar
  • Oxidation - Oxidized to carboxyl/COOH
  • Reduction - Reduced to sugar alcohol
  • monosaccharides do not usually exist in solution in their "open-chain" forms
  • an alcohol group can add into the carbonyl group in the same molecule to form a pyranose ring containing a stable hemiacetal (aldehyde) or hemiketal (ketone)
  • Haworth projection is a common way of writing a structural formula of sugars (monosaccharides and disaccharides) with an unpretentious three-dimensional perspective. Pyranose Ring (piattos)
  • **Formation of Phosphate Esters
  • Phosphate Esters**
  • a class of organophosphorus compounds with the general structure O=P(OR) 3, a central phosphate molecule with alkyl or aromatic substituents.
  • phosphate esters can form at the 6-carbon of aldohexose and ketohexose
  • sugar-phosphate backbone of DNA & RNA, ATP
  • **Monosaccharide derivatives
  • Deoxy sugars**
  • Sugars that have had hydroxyl group replaced with hydrogen atom - Amino sugars
  • Sugars where hydroxyl group is replaced with an amino group - Alcohol sugars
  • Polyhydric alcohols (polyols) formed when the carbonyl group of the monosaccharide is reduced to hydroxyl group (one -OH/hydroxyl group attached to each carbon) - Carboxylic Acid sugars
  • A carbonyl or hydroxyl group is oxidized to a carboxylic acid group
  • Common Monosaccharides
  • Glucose
  • Fructose
  • Galactose B. Oligosaccharides
  • Contain 2-10 monosaccharide units C. Disaccharides
  • Two monosaccharides linked together through a glycosidic linkage