Chapter 24

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30 Terms

1
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- polyamides of a alpha-amino acids
- there are approximately 20 natural alpha-amino acids

What are proteins?

2
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- the exact sequence of the different alpha-amino acids

What is the primary structure of proteins?

3
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- amide bonds

What are proteins linked together with?

4
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- regions of ordered structures within a protein

What are secondary structures of proteins?

5
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- alpha-Helices
- beta-sheets
- beta-turns

What are some examples of secondary structures of proteins?

6
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- the overall three-dimensional shape of proteins

What are tertiary structures of proteins?

7
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- the arrangement of the subunits in proteins that consist of several peptide chains

What are quaternary structures of proteins?

8
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4 subunits
- alpha chains are 141 amino acid lengths and beta chains contain 146 amino acids

What do hemoglobin consist of?

9
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- 2 polypeptide chains which are covalently linked with disulfide bonds

What does bovine insulin consist of?

10
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- an acidic side chain which is deprotonated at neutral pH

Describe the side chain of aspartic acid?

11
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- a basic amino group that will be protonated at neutral pH

Describe the amino group of lysine?

12
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- zwitterion: has a net charge of 0

What is this molecule and describe?

<p>What is this molecule and describe?</p>
13
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- is the pH at with an amino acid carries a net zero charge

What is the isoelectric point pI?

14
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- 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?

15
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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?

<p>***What is the name of this reaction and what are the reagents?</p>
16
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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?

<p>***What is the name of this reaction and what are the reagents?</p>
17
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Strecker synthesis
- NH4Cl, NaCN
- H3O+

***What is the name of this reaction and what are the reagents?

<p>***What is the name of this reaction and what are the reagents?</p>
18
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peptide bond formation via activated ester
- DCC

What is the name of this reaction and what are the reagents?

<p>What is the name of this reaction and what are the reagents?</p>
19
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- Boc protecting group

What is the name of this protecting group?

<p>What is the name of this protecting group?</p>
20
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deprotection
- CF3CO2H or HCl

***What is the name of this reaction and what are the reagents?

<p>***What is the name of this reaction and what are the reagents?</p>
21
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- Fmoc

What is the name of this protecting group?

<p>What is the name of this protecting group?</p>
22
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deproteciton with Fmoc
- piperidine, DMF

***What is the name of this reaction and what are the reagents?

<p>***What is the name of this reaction and what are the reagents?</p>
23
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- Cbz

What is the name of this protecting group?

<p>What is the name of this protecting group?</p>
24
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Deprotection of Cbz
- H2, Pd/C

What is the name of this reaction and what are the reagents?

<p>What is the name of this reaction and what are the reagents?</p>
25
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- protection of a carboxylic acid as ester (fisher esterification)

This reaction is an example of what?

<p>This reaction is an example of what?</p>
26
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- deprotection of a benzyl ester

This reaction is an example of what?

<p>This reaction is an example of what?</p>
27
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- trityl or tert-butyl

What are good protecting groups for cysteine?

28
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- benzyl ethers
- tert-butyl

What are good protecting groups for serine, threonine, and tyrosine

29
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- Boc
- trityl

What are good protecting groups for lysine, histidine, and tryptophan?

30
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- esters

What are good protecting groups for aspartic acid and glutamic acid?