27.14 The Strategy of Peptide Synthesis
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1 27.14 The Strategy of Peptide Synthesis
2 General Considerations Making peptide bonds between amino acids is not difficult. The challenge is connecting amino acids in the correct sequence. Random peptide bond formation in a mixture of phenylalanine and glycine,, for example, will give four dipeptides. Phe Phe Gly Gly Phe Gly Gly Phe
3 General Strategy 1. Limit the number of possibilities by "protecting" the nitrogen of one amino acid and the carboxyl group of the other. N-Protected phenylalanine C-Protected glycine X NH H 2 N 2 C Y C 6 H 5
4 General Strategy 2. Couple the two protected amino acids. X NHC NH 2 C Y C 6 H 5 X NH H 2 N 2 C Y C 6 H 5
5 General Strategy 3. Deprotect the amino group at the N-terminus N and the carboxyl group at the C-terminus. C X NHC NH 2 C Y C 6 H 5 + H 3 NC NH 2 C C 6 H 5 Phe-Gly
6 27.15 Amino Group Protection
7 Protect Amino Groups as Amides Amino groups are normally protected by converting them to amides. Benzyloxycarbonyl (C 6 H 5 ) ) is a common protecting group. It is abbreviated as Z. Z-protection is carried out by treating an amino acid with benzyloxycarbonyl chloride.
8 Protect Amino Groups as Amides CCl + + H 3 NC C 6 H 5 C 1. NaH, H 2 2. H + NH C 6 H 5 (82-87%) 87%)
9 Protect Amino Groups as Amides C NH C 6 H 5 is abbreviated as: ZNH or Z-PheZ C 6 H 5
10 Removing Z-ProtectionZ An advantage of the benzyloxycarbonyl protecting group is that it is easily removed by: a) hydrogenolysis b) cleavage with HBr in acetic acid
11 Hydrogenolysis of Z-Protecting Z Group C NHCNHH C 2 3 C 6 H 5 H 2, Pd 3 C 2 H 2 NCNHH C 2 3 C 6 H 5 (100%)
12 HBr Cleavage of Z-Protecting Z Group C NHCNHH C 2 3 C 6 H 5 HBr Br C 2 + H 3 NCNHH C 2 3 C 6 H 5 Br (82%)
13 The tert-butoxycarbonyl Protecting Group ( 3 ) 3 CC NH C 6 H 5 is abbreviated as: BocNH or Boc-Phe C 6 H 5
14 HBr Cleavage of Boc-Protecting Group ( 3 ) 3 CC NHCNHH C 2 3 C 6 H 5 HBr H 3 C H 3 C C C 2 + H 3 NCNHH C 2 3 C 6 H 5 Br (86%)
15 27.16 Carboxyl Group Protection
16 Protect Carboxyl Groups as Esters Carboxyl groups are normally protected as esters. Deprotection of methyl and ethyl esters is by hydrolysis in base. Benzyl esters can be cleaved by hydrogenolysis.
17 Hydrogenolysis of Benzyl Esters C 6 H 5 C NHCNHH C C 6 H 5 C 6 H 5 H 2, Pd C 6 H 5 3 C 2 + H 3 NCNHH C 3 C 6 H 5 C 6 H 5 (87%)
18 27.17 Peptide Bond Formation
19 Forming Peptide Bonds The two major methods are: 1. coupling of suitably protected amino acids using N,N' N'-dicyclohexylcarbodiimide (DCCI) 2. via an active ester of the N-terminal N amino acid.
20 DCCI-Promoted Coupling ZNH C 6 H 5 + H 2N 2 C 3 DCCI, chloroform ZNHC NH 2 C 3 C 6 H 5 (83%)
21 Mechanism of DCCI-Promoted Coupling ZNH C 6 H 5 + C 6 H 11 N C NC 6 H 11 H C 6 H 11 N C C 6 H 11 N CNHZ HZ C 6 H 5
22 Mechanism of DCCI-Promoted Coupling The species formed by addition of the Z-Z protected amino acid to DCCI is similar in structure to an acid anhydride and acts as an acylating agent. Attack by the amine function of the carboxyl- protected amino acid on the carbonyl group leads to nucleophilic acyl substitution. H C 6 H 11 N C C 6 H 11 N CNHZ HZ C 6 H 5
23 Mechanism of DCCI-Promoted Coupling H C 6 H 11 N C C 6 H 11 NH + ZNHC C 6 H 5 NH 2 C 3 H 2 N 2 C 3 H C 6 H 11 N C C 6 H 11 N CNHZ HZ C 6 H 5
24 The Active Ester Method A p-nitrophenyl ester is an example of an "active ester." p-nitrophenyl is a better leaving group than methyl or ethyl, and p-nitrophenyl esters are more reactive in nucleophilic acyl substitution.
25 The Active Ester Method ZNHC C 6 H 5 N 2 + H 2 N 2 C 3
26 The Active Ester Method ZNHC C 6 H 5 N 2 + H 2 N 2 C 3 chloroform ZNHC NH 2 C 3 + H N 2 C 6 H 5 (78%)
27 27.18 Solid-Phase Peptide Synthesis: The Merrifield Method
28 Solid-Phase Peptide Synthesis In solid-phase synthesis, the starting material is bonded to an inert solid support. Reactants are added in solution. Reaction occurs at the interface between the solid and the solution. Because the starting material is bonded to the solid, any product from the starting material remains bonded as well. Purification involves simply washing the byproducts from the solid support.
29 The Solid Support The solid support is a copolymer of styrene and divinylbenzene. It is represented above as if it were polystyrene. Cross-linking with divinylbenzene simply provides a more rigid polymer.
30 The Solid Support Treating the polymeric support with chloromethyl methyl ether (Cl 3 ) and SnCl 4 places Cl side chains on some of the benzene rings.
31 The Solid Support Cl The side chain chloromethyl group is a benzylic halide, reactive toward nucleophilic substitution (S N 2).
32 The Solid Support Cl The chloromethylated resin is treated with the Boc- protected C-terminal C amino acid. Nucleophilic substitution occurs, and the Boc-protected amino acid is bound to the resin as an ester.
33 The Merrifield Procedure BocNHC Cl R
34 The Merrifield Procedure BocNHC Next, the Boc protecting group is removed with HCl. R
35 The Merrifield Procedure H 2 NC DCCI-promoted coupling adds the second amino acid R
36 The Merrifield Procedure BocNHC NHC R' R Remove the Boc protecting group.
37 The Merrifield Procedure H 2 NC NHC R' R Add the next amino acid and repeat.
38 The Merrifield Procedure + H 3 N peptide C NHC NHC R' R Remove the peptide from the resin with HBr in CF 3 C 2 H
39 The Merrifield Procedure + H 3 N peptide C NHC NHC Br R' R
40 The Merrifield Method Merrifield also automated his solid-phase method. Synthesized a nonapeptide (bradykinin) in 1962 in 8 days in 68% yield. Synthesized ribonuclease (124 amino acids) in reactions; 11,391 steps Nobel Prize in chemistry: 1984
2. Couple the two protected amino acids.
General Considerations The Strategy of Peptide Synthesis Making peptide bonds between amino acids is not difficult. The challenge is connecting amino acids in the correct sequence. andom peptide bond formation
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