amino acids met dank aan dr. detke. most amino acids are chiral all naturally occuring amino acids...

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Amino acids Met dank aan Dr. Detke

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Page 1: Amino acids Met dank aan Dr. Detke. Most amino acids are chiral All naturally occuring amino acids except Gly are the L isomer L & D amino acids are stereoisomers

Amino acids

Met dank aan Dr. Detke

Page 2: Amino acids Met dank aan Dr. Detke. Most amino acids are chiral All naturally occuring amino acids except Gly are the L isomer L & D amino acids are stereoisomers

Most amino acids are chiral All naturally occuring amino acids

except Gly are the L isomer L & D amino acids are stereoisomers

Page 3: Amino acids Met dank aan Dr. Detke. Most amino acids are chiral All naturally occuring amino acids except Gly are the L isomer L & D amino acids are stereoisomers

Most amino acids are zwitterions amino acids

are zwitterions at neutral pH (contains negative and positive charged groups)

Page 4: Amino acids Met dank aan Dr. Detke. Most amino acids are chiral All naturally occuring amino acids except Gly are the L isomer L & D amino acids are stereoisomers

Small aliphatic amino acids Glycine

non-chiral smallest most flexible in

polypeptides less hydrophobic

Alanine chiral next smallest less hydrophobic

Page 5: Amino acids Met dank aan Dr. Detke. Most amino acids are chiral All naturally occuring amino acids except Gly are the L isomer L & D amino acids are stereoisomers

Other aliphatic amino acids

Val, Leu, Ile Highly hydrophobic branched side-chains

Page 6: Amino acids Met dank aan Dr. Detke. Most amino acids are chiral All naturally occuring amino acids except Gly are the L isomer L & D amino acids are stereoisomers

Yet another aliphatic amino acid

Proline imino acid rigid ring structure puts kinks in

polypeptides

Page 7: Amino acids Met dank aan Dr. Detke. Most amino acids are chiral All naturally occuring amino acids except Gly are the L isomer L & D amino acids are stereoisomers

Aromatic amino acidsPhenylalanine•Absorbs UV•Very hydrophobic

Tyrosine•Absorbs UV•less hydrophobic•H-bonds•OH can ionize•OH can be modified

Tryptophan•Really absorbs UV!•less hydrophobic•H-bonds

Page 8: Amino acids Met dank aan Dr. Detke. Most amino acids are chiral All naturally occuring amino acids except Gly are the L isomer L & D amino acids are stereoisomers

Sulfur-containing amino acids

Methionine highly hydrophobic initiator amino acid

Cysteine less hydrophobic forms disulfide bonds SH group can ionize

Page 9: Amino acids Met dank aan Dr. Detke. Most amino acids are chiral All naturally occuring amino acids except Gly are the L isomer L & D amino acids are stereoisomers

Oxidation of cysteine to cystine

Disulfide bond formation is reversible

Disulfide bonds form in proteins and help stabilize their structures

Page 10: Amino acids Met dank aan Dr. Detke. Most amino acids are chiral All naturally occuring amino acids except Gly are the L isomer L & D amino acids are stereoisomers

Alcoholic amino acids

Ser, Thr less hydrophobic H-bonding potential can be modified Thr is an isostere of

Val

Page 11: Amino acids Met dank aan Dr. Detke. Most amino acids are chiral All naturally occuring amino acids except Gly are the L isomer L & D amino acids are stereoisomers

Acidic amino acids

Asp, Glu highly

hydrophilic negatively

charged at neutral pH

Page 12: Amino acids Met dank aan Dr. Detke. Most amino acids are chiral All naturally occuring amino acids except Gly are the L isomer L & D amino acids are stereoisomers

Basic amino acids Highly hydrophilic Lys and Arg are positively charged at neutral pH His is partially charged at neutral pH

Page 13: Amino acids Met dank aan Dr. Detke. Most amino acids are chiral All naturally occuring amino acids except Gly are the L isomer L & D amino acids are stereoisomers

Amide-containing amino acids

Asn, Gln highly hydrophilic H-bonding potential isosteres of Asp and

Glu

Page 14: Amino acids Met dank aan Dr. Detke. Most amino acids are chiral All naturally occuring amino acids except Gly are the L isomer L & D amino acids are stereoisomers

Peptide bond formation

Page 15: Amino acids Met dank aan Dr. Detke. Most amino acids are chiral All naturally occuring amino acids except Gly are the L isomer L & D amino acids are stereoisomers

The peptide bond is planar

Fig. 4.6

Page 16: Amino acids Met dank aan Dr. Detke. Most amino acids are chiral All naturally occuring amino acids except Gly are the L isomer L & D amino acids are stereoisomers

Aspartame – a dipeptide

200X Sweeter than Sucrose !!!

aspartylphenylalanine methyl ester