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and Proteins.
Classification of Amino Acids
Fundamentals
+
NH3 an a-amino acid that is an
intermediate in the biosynthesis
a
CO2
of ethylene
H O
+
H3N C C O
H O
+
Glycine H3N C C O
(Gly or G)
H
H O
+
H3N C C O
CH3
Alanine
(Ala or A)
Table 27.1
H O
+
H3N C C O
CH(CH3)2
Valine
(Val or V)
Table 27.1
H O
+
H3N C C O
CH2CH(CH3)2
Leucine
(Leu or L)
Table 27.1
H O
+
H3N C C O
CH3CHCH2CH3
Isoleucine
(Ile or I)
Table 27.1
H O
+
H3N C C O
CH3SCH2CH2
Methionine
(Met or M)
Table 27.1
H O
+
H2N C C O
H2C CH2
C
H2
Proline
(Pro or P)
Table 27.1
H O
+
H3N C C O
CH2
Phenylalanine
(Phe or F)
Table 27.1
H O
+
H3N C C O
CH2
Tryptophan
N (Trp or W)
H
Table 27.1
H O
+
H3N C C O
H2NCCH2
Asparagine
(Asn or N)
Table 27.1
H O
+
H3N C C O
H2NCCH2CH2
Glutamine
(Gln or Q)
Table 27.1
H O
+
H3N C C O
CH2OH
Serine
(Ser or S)
Table 27.1
H O
+
H3N C C O
CH3CHOH
Threonine
(Thr or T)
Table 27.1
H O
+
H3N C C O
OCCH2
Aspartic Acid
(Asp or D)
Table 27.1
H O
+
H3N C C O
OCCH2CH2
Glutamic Acid
(Glu or E)
Table 27.1
H O
+
H3N C C O
CH2
Tyrosine
(Tyr or Y)
OH
Table 27.1
H O
+
H3N C C O
CH2SH
Cysteine
(Cys or C)
Table 27.1
H O
+
H3N C C O
+
CH2CH2CH2CH2NH3
Lysine
(Lys or K)
Table 27.1
H O
+
H3N C C O
CH2CH2CH2NHCNH2
+ NH2
Arginine
(Arg or R)
Table 27.1
H O
+
H3N C C O
CH2
N NH
Histidine
(His or H)
27.2
Stereochemistry of Amino Acids
Configuration of a-Amino Acids
R
27.7
Peptides
Peptides
H O H O
+ +
H3N C C O H3N C C O
CH3 H
Alanylglycine
H O H O
+
H3N
C C N C C O
CH3 H H
H O H O
+
H3N
C C N C C O
CH3 H H
N-terminus C-terminus
AlaGly
AG
Alanylglycine and glycylalanine are
constitutional isomers
H O H O
+ Alanylglycine
H3N
C C N C C O AlaGly
AG
CH3 H H
H O H O
+ Glycylalanine
H3N GlyAla
C C N C C O
GA
H H CH3
Alanylglycine
H O H O
+
H3N
C C N C C O
CH3 H H
TyrGlyGlyPheLeu
YGGFL
Oxytocin
4 5
3
IleGlnAsn C-terminus
2
Tyr CysProLeuGlyNH2
6 7 8 9
1
Cys S S
N-terminus
Oxytocin is a cyclic nonapeptide.
Instead of having its amino acids linked in an
extended chain, two cysteine residues are
joined by an SS bond.
Oxytocin
SS bond