How To Make A Peptide
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1 1 Manickam Sugumaran Department of iology University of Massachusetts oston, M Conventional synthesis
2 2 Synthesis of peptide by conventional method Time consuming Laborious Complicated purification needed Low yield Solid Phase Synthesis
3 In Solid Phase Synthesis, Products Can e Isolated Easily y Filtration C F G D C F G Filteration E I D E I Solid Phase Synthesis -dvantages Reaction can be forced to go towards 100% yield by excess reagents. Recovery of the products are easy - Simple filtration as opposed to complicated precipitation and recrystallization. Purification of products is easy - simple wash. Several steps can be accomplished on the same resin. In general, large scale saving in time, effort and reagents. 3
4 Steps Involved in a Dipeptide Synthesis Protect the amino group of first amino acid Protect the carboxyl group of second amino acid ctivate the carboxyl group of first amino acid φ 2 2 C C C φ 2 φ C CX C Couple them φ C + 2 CX φ C CX Deblock the protecting group φ C CX 2 C C X Solid support with a functional group ttach first amino acid ttach second amino acid Continue the process eave the peptide 4
5 Resin made by copolymerizing styrene and 1% divinylbenzene Resins (other than polystyrene) used in solid phase synthesis : Polymethylmethacrylates polyacrylamides Phenolic resins Polysaccharides Inorganic supports such as Silica and Porous glass 5
6 First: Functionalizing the resin C 3 C 2 Zn 2 Step -1: nchoring the first amino acid - The first t-oc amino acid is attached via benzylester group to the insoluble resin. + Cs C nchor the first amino acid C 6
7 Step-2: Deprotection of the amino group - t-oc is completely removed by 50%TF in dichloromethane, while the benzyl ester is untouched. C Deprotect the amino group CF 3 C C 3 Step 3: Deprotonation - Tertiary amines, (diisopropyl ethyl amine) deprotonate the salt. C 3 Deprotonate R 3 C 2 7
8 Step 4: Coupling the next amino acid - Dicyclohexylcarbodiimide activates the carboxyl group of the second amino acid and allows the coupling to the first amino acid. Water is extracted to form dicyclohexylurea. C 2 + C Couple =C= C C Mechanism of coupling reaction t-c-amino acid + Dicyclohexylcarbodiimide C Dicyclohexylurea + 2 C ctivated amino acid Dipeptide X X 8
9 Step 5: Continue peptide synthesis C C C Repeat Steps 2,3,4 C Tripeptide R 3 C Step 6: eave the peptide from resin - Finally the free peptide is liberated from the resin by a strong acid such as F. R 3 C C C Tripeptide eave the peptide F C C C Tripeptide R 3 2 9
10 R 3 Deprotonate C C 3 C 2 C 3 Zn 2 3 Deprotect the amino group C =C= + 2 Couple 4 C = Cs C nchor the first amino acid 2 CF 3 C eave the peptide C 2 C C C F Trimeric peptide Repeat Steps 2,3,4 Solid phase synthesis ruce Merrifield synthesized Ribonuclease (124 amino acid) and interferon (155 amino acid) using solid phase peptide synthesis. 10
11 DVTGE: SYTESIS F YDRPIC PEPTIDES 2 eyond tetrapeptide aggregation and precipitation prevents further synthesis in solution 2 I SLID PSE, CTISLEUCIE D EVE DDECYL ISLEUCIE VE EE SUCCESSFULLY SYTESIZED For a 50 amino acid peptide synthesis, how coupling efficiency at each step affects the final purity of the product. CUPLIG EFFICIECY (%) PURITY F PRDUCT (%)
12 cyloxymethyl-pam-resin Insertion of acetamidomethyl group (green) in between the benzyl ester and polystyrene resin increased the stability of benzyl ester to trifluoroacetic acid by about 400 times. R Use of photolabile resin as a mean to remove the synthesized peptide R hν 2 12
13 Different protecting groups Photolabile group at the first linkage site. t-c for protection of side chains. Thiol labile group for protection of -terminals. 2 hν TF TF S S RS T VID TE S1 RECTI, SE (DIMETYLSULFIDE) IS DDED T F I 1:1 RTI. TIS FRCES TE CLEVGE T S2 RECTI D PREVETS TE EZYL CTI FRM TTCKIG TE PEPTIDE. 13
14 2 F 2 S 1 2 C 2 REID SME WERE ELSE TE PEPTIDE 2 S F S 2 S 2 2 C 2 S 14
2. Couple the two protected amino acids.
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DETERMINACIÓN DE ESTRUCTURAS ORGÁNICAS (ORGANIC SPECTROSCOPY) PURIFICATION TECHNIQUES Hermenegildo García Gómez Departamento de Química Instituto de Tecnología Química Universidad Politécnica de Valencia