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Gurpreet Singh

M.Pharmacy(Pharmaceutics)
AMINO ACIDS: PROPERTIES AND STRUCTURE Guru Nanak Dev University
e-mail. surtall3@yahoo.co.in

Proteins are composed of 20 different amino acids which are


distinguished by their side-chain groups, designated as R (see figure at
right). The amino acids are grouped below according to the chemical
nature of their side-chain groups.

Name/Abbreviations R-group Comments


The lack of a side chain provides for the
Glycine Gly G -H greatest possible conformational
flexibility.
The aliphatic side-chain forms a cyclic
imino compound (entire amino acid is
Proline Pro P shown). This imposes rigid constraints on
the rotation around the backbone and has
significant affects on protein conformation.
Amino Acids with Aliphatic Side Chains
Alanine Ala A -CH3
Valine Val V These alkyl side-chain groups are
important for hydrophobic interactions and
Leucine Leu L provide for a variety of surfaces and
shapes.
Isoleucine Ile I
Amino Acids with Aromatic Side Chains

Phenylalanine Phe F
The aromatic groups are important for
Tyrosine Tyr Y hydrophobic interactions and may be
especially important for interacting with
other flat molecules.
Tryptophan Trp W

Amino Acid Alcohols


Serine Ser S -CH2OH The hydroxyl groups are weakly ionizable
(pKa~13) and participate as active groups
Threonine Thr T in some enyzmes.
Acidic Amino Acids
Aspartatic acid Asp D These side-chain groups are generally
negatively charged at neutral pH (pKa =
Glutamatic 4.3-4.7).
Glu E -CH2CH2CO2H
acid

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Gurpreet Singh
M.Pharmacy(Pharmaceutics)
Guru Nanak Dev University
e-mail. surtall3@yahoo.co.in

Amides of the Acidic Amino Acids


Asparagine Asn N These side-chain groups do not ionize, but
are relatively polar.
Glutamine Gln Q -CH2CH2CONH2
Basic Amino Acids
The imidazole group participates in the
Histidine His H active site of many enzymes, as well as
binding metal ions.
Lysine Lys K -CH2CH2CH2CH2NH2
These side-chain groups are generally
Arginine Arg R positively charged at neutal pH (pKa >10).

Sulfur Containing Amino Acids


-CH2SH Cysteines participate in redox reactions
Cysteine Cys C -CH2S- and can form disulfide links between two
SCH2- residues (i.e., oxidized state).
Met is rather hydrophobic, but the
Methionine Met M -CH2CH2SCH3
thioether group is a potent nucleophile.
Other Abbreviations
Asp or Asn Asx B The amides are converted to the acids by the procedures used to
identify and quantify amino acid residues. Therefore they are
Glu or Gln Glx Z designated as either in such situations..
Any amino
Xaa X Used when the amino acid is unknown or does not matter.
acid

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