amino acids Flashcards
Absolute configuration at the alpha carbon position
the alpha carbon in every amino acid is a chiral center (except in glycine, which is achrial)
every amino acid has S configuration except for cysteine, which is R configuration
Effect of pH on amino acids
Amino acids are dipolar ions
at low pH they are positively charged (cationic)
at high pH they are negatively charged (anionic)
at pH=pI they are zwitterionic (neutral)
acidic amino acids
aspartic acid (Asp, D) and glutamic acid (Glu, E)
basic amino acids
histidine (His, H), arginine (Arg, R), and lysine (Lys, K)
polar amino acids
cysteine (Cys, C), asparagine (Asn, N), gutamine (Gln, Q), threonine (Thr, T), serine (Ser, S), and tyrosine (Tyr, Y)
(CNQTS, Y?)
non-polar amino acids
leucine (Leu, L), isoleucine (Ise, I), methionine (Met, M), proline (Pro, P), valine (Val, V), alanine (Ala, A), glycine (Gly, G), phenylalanine (Phe, F), and tryptophan (Trp, W)
sulfur linkage
disulfide bond forms between two cysteins
peptide linkage
peptide bonds link amino acids together
formed by nucleophilic addition-elimination (condensation / dehydration reaction) between the carboxyl group of one amino acid and the amino group of another amino acid
nucleophilic amino group attacks the electrophilic carbonyl
peptide bond has resonance delocalization, making bond rigid and planar although there is still free rotation around the alpha carbon
hydrolysis
reaction that breaks peptide bond
nonspecific: acid/base hydrolysis breaks bond
specific: proteolytic enzymes break bond