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Lecture notes MCB2021F (MCB2021F)

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This module covers general properties of amino acids, stereochemistry of amino acids, acid/base properties of amino acids and analysis of amino acids.

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  • June 22, 2022
  • 12
  • 2021/2022
  • Class notes
  • Thomas oelgeschlager
  • All classes

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🧪
Amino Acids
General Properties
The four most abundant elements in living organisms - CHON

The six most essential elements of life - CHNOPS

Tetrahedral carbon
tetravalent - four electrons available to form covalent bonds

tetrahedral geometry - central carbon with four single bonds pointing away from
each other at the same angle = 109,5 degrees

Double and Triple bonds
Double bonds:

Atoms participating at double bond
cannot freely rotate.

Double/Triple bond is planar

In cases where carbon atoms
engage in two double bonds or a
triple bonds plus a single bond is
linear




Catenation - the ability of a
chemical element (carbon
structures) to form long chain-like
structures via a series of covalent
bonds




Amino Acids 1

, Chirality
alpha-carbon is
chiral/assymetrical/stereocenter
when four different chemical groups
is attached to it.

Enantiomers - superimposable
mirror images of each other

Skeletal formula - only carbon
atoms and functional groups (no
hydrogens)




In the absense of an ionizable side chain (R-group) amino acids exist at neutral
pH as a zwitterion/dipolar ion, which can act as either an acid (H donor) or base
(H acceptor).

At neural pH - protonated positively charged amino group and deprotonated
negatively charged carboxyl group.

Amphoteric/Ampholytes - molecules with dual base/acid properties

Low pH → protonated amino group; net charge = +1

High pH → deprotonated carboxylic acid; net charge = -1

Peptide bond is formed when alpha-carboxyl and alpha-amino groups of two
amino acids react in a condensation reaction, releasing one molecule of H20 =
dipeptide



Classification


Amino Acids 2

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