Chem 109 C Fall 2014 Armen Zakarian Office: Chemistry Bldn 2217
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1 Chem 109 C Fall 2014 Armen Zakarian ffice: Chemistry Bldn 2217! 1
2 Amino acids: Resolution of Racemates 2
3 Peptides/Proteins: Peptide Bonds peptides: formed from simple amino acids through peptide bonds 3
4 Peptides/Proteins: Peptide Bonds peptides: formed from simple amino acids through peptide bonds - 4
5 Peptides/Proteins: Peptide Bonds peptides: formed from simple amino acids through peptide bonds - - 5
6 Peptides/Proteins: Peptide Bonds peptides: formed from simple amino acids through peptide bonds -terminal aa C-terminal aa - - 6
7 Peptides/Proteins: Peptide Bonds peptides: formed from simple amino acids through peptide bonds -terminal aa C-terminal aa - - if sequence known Phe-Ser-Leu-Leu FSLL Leu-Ser-Phe-Leu LSFL 7
8 Peptides/Proteins: Peptide Bonds peptides: formed from simple amino acids through peptide bonds -terminal aa C-terminal aa - - if sequence known Phe-Ser-Leu-Leu FSLL Leu-Ser-Phe-Leu LSFL if sequence unknown Leu, Phe, Ser Leu, Phe, Ser 8
9 Peptides/Proteins: Peptide Bonds!-carbon R - R + R R peptide bond: about 40% double bond character restricted rotation s-trans is more stable R R R R s-trans strongly FAVRED s-cis strongly disfavored 9
10 Peptides/Proteins: Peptide Bonds colored squares - planar where is free rotation? 10
11 Peptides/Proteins: Peptide Bonds PRBLEM 24 Draw the tetrapeptide Ala-Thr-Asp-Asn and indicate the peptide bonds 11
12 Peptides/Proteins: Peptide Bonds PRBLEM Using the three-letter abbreviations, write the six tripeptides consisting of Ala, Gly, and Met. 12
13 Peptides/Proteins: Disulfide Bonds mild oxidant 2 R S R S S R a thiol a disulfide disulfide bridge 13
14 Peptides/Proteins: Disulfide Bonds 14
15 Peptides/Proteins: Some Interesting Peptides endorphines: 15
16 Peptides/Proteins: Some Interesting Peptides endorphines: fight-or-flight hormone: Cys-Tyr-Phe-Gln-Asn-Cys-Pro-Arg-Gly- 2 S S vasopressin 16
17 Peptides/Proteins: Some Interesting Peptides endorphines: fight-or-flight hormone: Cys-Tyr-Phe-Gln-Asn-Cys-Pro-Arg-Gly- 2 social bonding hormone: S S vasopressin Cys-Tyr-Ile-Gln-Asn-Cys-Pro-Leu-Gly- 2 S S oxytocin 17
18 -protection C-activation 18
19 -protection C-activation
20 Making Gly-Ala Step 1. Protect of Gly 20
21 Making Gly-Ala Step 1. Protect of Gly Step 2. Activating -protected Gly 21
22 Making Gly-Ala Step 1. Protect of Gly Step 2. Activating -protected Gly Step 3. Adding Ala 22
23 Making Gly-Ala Step 1. Protect of Gly Step 2. Activating -protected Gly Step 3. Adding Ala Step 4. Deprotection - mission completion 23
24 overall yield for the attachment of amino acids: number of amino acids overall yield 80% 64% 51% 41% 33% 26% 21% 17% 24
25 PRBLEM Show the steps in the synthesis of Leu-Phe-Lys-Val 25
26 PRBLEM Calculate the overall yield of bradykinin when the yield for the addition of each amino acid to the chain is 70%. Arg-Pro-Pro-Gly-Phe-Ser-Pro-Phe-Arg! 26
27 Merrifield automated synthesis 27
28 Merrifield automated synthesis 28
29 Merrifield automated synthesis 29
30 Merrifield automated synthesis 30
31 Merrifield automated synthesis 31
32 Merrifield automated synthesis 32
33 Merrifield automated synthesis 33
34 Merrifield automated synthesis 34
35 Merrifield automated synthesis 35
36 Merrifield automated synthesis 36
37 Merrifield automated synthesis 37
38 Merrifield automated synthesis overview of the Merrifield automated synthesis: synthesis on solid support, >98% yield per a.a. C to terminus nonapeptide bradykinin synthesized in 4 h and 85% overall yield limitation: up to a 100 amino acids 38
2. Couple the two protected amino acids.
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