Biochem 1: Amino Acids and Peptides Flashcards
an amino acid is
a compound that contains both an amino group and a carboxyl group (both are bonded to the alpha-carbon, the one next to the carboxyl group)
alpha carbon on amino acid
also bound to hydrogen and the side chain group R
what is the R group of an amino acid important for
determines identify of amino acid
stereoisomers of amino acids
designated L- or D-
stero properties of amino acids
with the exception of glycine, most amino acids are chiral (stereoisomers)
-the vast majority have L-configuration at the alpha carbon
non polar side chain amino acids
Ala, Val, Leu, Ile, Pro, Phe, Trp, Met, Gly
neutral polar side chain amino acids
Ser, Thr, Tyr, Cys, Gln, Asn
acidic side chain amino acids
Glu, Asp
basic side chains amino acids
His, Lys, Arg
what are amino acids (in terms of titrations)
are weak, diuretic (or triprotic) acids that can be titrated with base
what are the charges of the amino and carboxyl group
carboxyl group (-) and amino group (+) are charged at neutral pH
what is special about “free amino acids”
alpha-carbon and a-amino groups have titratable protons (some side chains so as well)
individual amino acids can be linked by forming
covalent bonds
peptide bonds
define peptide bond
the amide bond between the alpha-carboxyl group of one amino acid and alpha-amino group of another amino acid
peptide bonds between amino acids are formed by
dehydration synthesis
geometry of peptide bond
the four atoms of a peptide bond and the two alpha carbons joined to it lie in a plane with bond angles of 120 degrees about C and N
to account for this geometry, a peptide bond is most accurately represented as a
hybrid of two contributing structures
resonance structures
2 examples of biologically active peptides
aspartame: Asp-Phe-methyl ester
glutathione: gamma- Glu-Cys-Gly
glutathione: gamma- Glu-Cys-Gly
biologically active peptide
- tripeptide with an unusual gamma-carboy peptide bond linkage
- important reductant in cells, it helps to protect proteins from oxidative damage