Beruflich Dokumente
Kultur Dokumente
Proteins
BIOL420
ada D. Son
Outline
What are proteins?
Building blocks
Properties of Amino Acids
Uncommon Amino Acids
Reactions of Amino Acids
Protein Basics
Proteins are the most abundant biological
macromolecules, occurring in all cells and all
parts of cells.
pH = 7.4
Chirality
A chiral molecule is a type of molecule that
lacks an internal plane of symmetry and has a
non-superimposable mirror image.
The feature that is most often the cause of
chirality in molecules is the presence of an
asymmetric carbon atom
Two mirror images of a chiral molecule are
called enantiomers or optical isomers
Chirality
Chirality for Amino Acids
For all the common amino acids except glycine, the -
carbon is bonded to four different groups: a carboxyl group,
an amino group, an R group, and a hydrogen atom.
The -carbon atom is thus a chiral center. Because of the
tetrahedral arrangement of the bonding orbitals around
the -carbon atom, the four different groups can occupy
two unique spatial arrangements, and thus amino acids
have two possible stereoisomers.
Since they are nonsuperimposable mirror images of each
other, the two forms represent a class of stereoisomers
called enantiomers. All molecules with a chiral center are
also optically activethat is, they rotate plane-polarized
light.
Determining the D/L isomeric form of
an Amino Acid
the "CORN" rule
The groups: COOH, R, NH2 and H (where R is a
variant carbon chain)are arranged around the
chiral center carbon atom.
Sighting with the hydrogen atom away from
the viewer, if these groups are arranged
clockwise around the carbon atom, then it is
the D-form.
If counter-clockwise, it is the L-form.
The D and L
enantiomers
for the amino
acid,
Alanine.
Chirality
In Biological systems L-form of the amino acids is
prefered.
D-alanine and D-glutamate are first discovered in
short peptides of cell walls of Gram-negative bacteria.
D-valine is present in peptide antibiotics:
valinomycine, actinomycin D, gramicidin A.
D-aspartate is isolated in human teeth, eye lenses,
erythrocytes and some tumors.
D-serine is isolated from mammalian brain where it
functions as neurotransmitter.
Amino Acids Can Be Classified by R Group
Nonpolar, Aliphatic R Groups The R groups in this class of
amino acids are nonpolar and hydrophobic.
www.ull.chemistry/uakron/bio
chem/04
22nd amino acid
Monomethylamine
methyltransferase enzyme
of a freshwater bacteria
contains this amino acid.
www.ull.chemistry/uakron/bio
chem/04
Selenocysteine is a special case. This rare amino acid
residue is introduced during protein synthesis rather than
created through a postsynthetic modification. It contains
selenium rather than the sulfur of cysteine. Actually
derived from serine, selenocysteine is a constituent of just
a few known proteins.