amino acids. naturally-occurring amino acids have l-configuration ….. with only a very few having...
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AMINO ACIDSAMINO ACIDS
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H
COOH
H2N
R
AMINO ACIDSAMINO ACIDS
Naturally-occurring amino acids have L-configuration
….. with only a very few having D-configuration
the R group varies
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Amino AcidsAmino Acids
D- L-
naturally-occurringamino acids are generally L-series
R R
COOH
NH2
COOH
H2NH H
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H
COOH
H2N
H
glycine - the only achiral amino acid
H
COOH
H2N
CH3
alanine
H
COOH
H2N
CHCH3 CH3
valine
R = H
R = CH3
R = CH(CH3)2
20 different ones occur in proteins
SOME EXAMPLE AMINO ACIDSSOME EXAMPLE AMINO ACIDS
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H
COOH
H2N
H
glycine - the only achiral amino acid
H
COOH
H2N
CH3
alanine
H
COOH
H2N
CHCH3 CH3
valine
R = H
R = CH3
R = CH(CH3)2
SOME EXAMPLE AMINO ACIDSSOME EXAMPLE AMINO ACIDS
20 different amino acids occur in proteins
They differ by the R group
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THE 20 COMMON AMINO ACIDSTHE 20 COMMON AMINO ACIDSAmino acids are classified by their R group
NON-POLAR
POLAR AMINO ACIDS
•NEUTRAL
•ACIDIC
•BASIC
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THE 9 NON-POLAR AMINO ACIDSTHE 9 NON-POLAR AMINO ACIDS
NH2 H
H
COOH
NH2 H
CH3
COOH
NH2 H
CH
COOH
CH3
CH3
NH2 H
CH2
COOH
CH CH3
CH3
NH2 H
CH
COOH
CH3
CH2
CH3
GlycineGly
AlanineAla
Valine*Val
Leucine*Leu
Isoleucine*Ile
NH2 H
COOH
CH2
NH2 H
COOH
CH2
NH
NH H
COOH
Phenylalanine*Phe
ProlinePro
Tryptophan*Trp
NH2 H
COOH
CH2
CH2 S CH3
Methionine*Met
* Essential amino acids
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THE 6 NEUTRAL POLAR AMINO ACIDSTHE 6 NEUTRAL POLAR AMINO ACIDS
NH2 H
COOH
CH2 OH
NH2 H
COOH
CH2
OH
NH2 H
COOH
CH OH
CH3
TyrosineTyr
serine Threonine*Thr
NH2 H
COOH
CH2
CO
NH2
NH2 H
COOH
CH2
CH2
CO
NH2
NH2 H
COOH
CH2 SH
AsparagineAsn
GlutamineGln
CysteineCys
* Essential amino acid
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NH2 H
COOH
CH2
COOH
NH2 H
COOH
CH2
CH2
COOH
aspartic acidAsp glutamic acid
Glu
THE ACIDIC AMINO ACIDSTHE ACIDIC AMINO ACIDS
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The Two Acidics
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THE BASIC AMINO ACIDSTHE BASIC AMINO ACIDS
NH2 H
CH2
COOH
CH2
CH2
CH2
NH2
NH2 H
CH2
COOH
CH2
CH2
NH
C NH
NH2
NH2 H
CH2
COOH
N
NH
Lysine*Lys
Histidine*His
Arginine*Arg
* Essential amino acids
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The Three Basics
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Which of the following compounds is an -amino acid?
1. Only (a)
2. (a) and (b)
3. (a) and (c)
4. (a) and (d)
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Which of the following compounds is an -amino acid?
1. Only (a)
2. (a) and (b)
3. (a) and (c)
4. (a) and (d)
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Which of the following amino acids is achiral?
1. Alanine 2. Aspargine3. Glycine4. Threonine
H O H O| || | ||
+H3N–C–C–O– +H3N–C–C–O–
| |CH3 H
Alanine, Ala Glycine, Gly
H O H O| || | ||
+H3N–C–C–O– +H3N–C–C–O–
| |CH2CNH2 CHCH3
|| |O OH
Asparagine, Asn Threonine, Thr
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Which of the following amino acids is achiral?
1. Alanine 2. Aspargine3. Glycine4. Threonine
H O H O| || | ||
+H3N–C–C–O– +H3N–C–C–O–
| |CH3 H
Alanine, Ala Glycine, Gly
H O H O| || | ||
+H3N–C–C–O– +H3N–C–C–O–
| |CH2CNH2 CHCH3
|| |O OH
Asparagine, Asn Threonine, Thr
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The amino acid shown below has a side chain that is
1. acidic2. basic3. nonpolar4. polar, neutral
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The amino acid shown below has a side chain that is
1. acidic2. basic3. nonpolar4. polar, neutral
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Which of the following amino acids can form hydrogen bonds between their side-chain groups?
1. Alanine and glycine2. Alanine and aspargine3. Aspargine and
threonine4. Glycine and threonine
H O H O| || | ||
+H3N–C–C–O– +H3N–C–C–O–
| |CH3 H
Alanine, Ala Glycine, Gly
H O H O| || | ||
+H3N–C–C–O– +H3N–C–C–O–
| |CH2CNH2 CHCH3
|| |O OH
Asparagine, Asn Threonine, Thr
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H O H O| || | ||
+H3N–C–C–O– +H3N–C–C–O–
| |CH3 H
Alanine, Ala Glycine, Gly
H O H O| || | ||
+H3N–C–C–O– +H3N–C–C–O–
| |CH2CNH2 CHCH3
|| |O OH
Asparagine, Asn Threonine, Thr
Which of the following amino acids can form hydrogen bonds between their side-chain groups?
1. Alanine and glycine2. Alanine and aspargine3. Aspargine and
threonine4. Glycine and threonine
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Unusual L-Amino Acids Found in Proteins
Fig. 3-8a