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- polyamides of a alpha-amino acids
- there are approximately 20 natural alpha-amino acids
What are proteins?
- the exact sequence of the different alpha-amino acids
What is the primary structure of proteins?
- amide bonds
What are proteins linked together with?
- regions of ordered structures within a protein
What are secondary structures of proteins?
- alpha-Helices
- beta-sheets
- beta-turns
What are some examples of secondary structures of proteins?
- the overall three-dimensional shape of proteins
What are tertiary structures of proteins?
- the arrangement of the subunits in proteins that consist of several peptide chains
What are quaternary structures of proteins?
4 subunits
- alpha chains are 141 amino acid lengths and beta chains contain 146 amino acids
What do hemoglobin consist of?
- 2 polypeptide chains which are covalently linked with disulfide bonds
What does bovine insulin consist of?
- an acidic side chain which is deprotonated at neutral pH
Describe the side chain of aspartic acid?
- a basic amino group that will be protonated at neutral pH
Describe the amino group of lysine?
- zwitterion: has a net charge of 0
What is this molecule and describe?
- is the pH at with an amino acid carries a net zero charge
What is the isoelectric point pI?
- all protein-derived amino acids have at least one stereogenic center, therefore chiral
- the vast majority of alpha-amino acids are L-amino acids with an S configuration
Describe the chirality of amino acids?
Synthesis of D/L-Phenylalanine from Phthalimidomalonic ester
- NaOEt
- Ar-Br
- NaOH
- H3O+ (HCl in H2O)
- delta
***What is the name of this reaction and what are the reagents?
Amino acid synthesis via the amidomalone synthesis
- NaOEt
- R-Br
- H3O+, delta (HCl in H2O)
***What is the name of this reaction and what are the reagents?
Strecker synthesis
- NH4Cl, NaCN
- H3O+
***What is the name of this reaction and what are the reagents?
peptide bond formation via activated ester
- DCC
What is the name of this reaction and what are the reagents?
- Boc protecting group
What is the name of this protecting group?
deprotection
- CF3CO2H or HCl
***What is the name of this reaction and what are the reagents?
- Fmoc
What is the name of this protecting group?
deproteciton with Fmoc
- piperidine, DMF
***What is the name of this reaction and what are the reagents?
- Cbz
What is the name of this protecting group?
Deprotection of Cbz
- H2, Pd/C
What is the name of this reaction and what are the reagents?
- protection of a carboxylic acid as ester (fisher esterification)
This reaction is an example of what?
- deprotection of a benzyl ester
This reaction is an example of what?
- trityl or tert-butyl
What are good protecting groups for cysteine?
- benzyl ethers
- tert-butyl
What are good protecting groups for serine, threonine, and tyrosine
- Boc
- trityl
What are good protecting groups for lysine, histidine, and tryptophan?
- esters
What are good protecting groups for aspartic acid and glutamic acid?