Resin solutions for peptide solid phase synthesis and purification. Alessandra Basso, PhD Lifetech Manager CPhI, Frankurt 24 October 2017

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1 Resin solutions for peptide solid phase synthesis and purification Alessandra Basso, PhD Lifetech Manager CPhI, Frankurt 24 October 2017

2 Over three decades, Purolite has grown into the world s premier resin technology manufacturer and innovation leader, with production plants and advanced research labs across the globe. 45+ Global Sales Offices 4 Production Plants 5 R&D Centers 1,400 Employees 2

3 Purolite Life Sciences product portfolio Purolite Life Sciences include the widest portfolio of resins for biotech applications. We develop standard and customized solutions for our customer needs. 3

4 Resins for Solid Phase Peptide Synthesis 4

5 Core resin Polystyrene is the most common core resin in solid phase chemistry: - High swelling in apolar solvents - Chemically stable Swelling factor of 1% crosslinked polystyrene in various solvents (ml/g of resin) Solvent Swelling (ml/g) Solvent Swelling (ml/g) THF 5.5 Et 2 O 3.2 Toluene 5.3 CH 2 CN 4.7 CH 2 Cl EtOH 5.0 Dioxane 4.9 MeOH 1.8 DMF 3.5 Water 1.0 (no swelling) 5

6 Chloromethyl Resin (Merrifield Resin) Particle size: mesh ( micron) Loading: mmol/g (after coupling with AA mmol/g) Advantages and use: - Substrates are attached to Merrifield resin by nucleophilic displacement of chlorine - Resin-substrate bond is acid stable and requires strong acid conditions for cleavage - Useful for SPPS and different applications as scavenger resins and polymer-supported reagents 6

7 Aminomethyl Resin (AM Resin) Particle size: mesh ( micron) Loading: mmol/g (after coupling with AA mmol/g) Advantages and use: - Aminomethyl (AM) resin has long been used in solid phase peptide synthesis as a core resin - various linkers can be attached through a stable amide bond 7

8 2-Chlorotrityl Chloride Resin (2-CTC) Particle size: mesh ( micron) Loading: mmol/g (after coupling with AA mmol/g) Advantages and use: - widely used in both solid phase organic and peptide chemistry - cleaved with acetic acid - particularly useful when less acid labile protecting groups are required on the substrate following cleavage - Bulky triphenylmethyl group prevents cyclization or racemization through steric hindrance - used to immobilize acids, alcohols and also amines or thiols - 2-chlorotrityl resin has better stability than the trityl resin 8

9 4-Benzyloxybenzyl Alcohol Resin (Wang resin) Particle size: mesh ( micron) Loading: mmol/g (after coupling with AA mmol/g) Advantages and use: - most widely used solid phase support for acid substrates - linker attached to the polystyrene core is 4-hydroxybenzyl alcohol - linkage has good stability to a variety of reaction conditions, but can be readily cleaved by moderate treatment with an acid, generally trifluoroacetic acid 9

10 4-Methylbenzhydrylamine Hydrochloride Salt Resin (MBHA Resin) Particle size: mesh ( micron) Loading: mmol/g (after coupling with AA mmol/g) Advantages and use: - originally developed for the formation of peptide amides using the Boc-N protection/tfa deprotection strategy - form very stable amide or amine linkages to either carboxylic or electrophilic alkyl substrates structurally similar to Rink - strong acid conditions are required to cleave substrates from these resins (hydrofluoric acid or trifluoromethanesulfonic acid (TFMSA)); therefore they are also used as base resins for anchoring linkers 10

11 Resins for peptide purification 11

12 Chromalite synthetic resins Products available Chromalite CGC and CGA cation and anion gel type activated styrene/polydivinylbenzene copolymer Chromalite MN - hyper-crosslinked polystyrene adsorbent Chromalite PCG - macroporous polydivinylbenzene adsorbent Chromalite AD - macroporous polydivinylbenzene adsorbent for analytical chromatography (5, 10 and 15 micron only) Chromalite MDEA anion activated methacrylate resin HPLC pre-packed columns Purophase SPE Reverse Phase NEW 12

13 Chromalite: particle size selection Chromalite size range Application 5 micron Analytical (HPLC) 10, 15 micron Preparative (HPLC) 15, 35, 50, 75 micron Process/polishing of proteins, small molecules and synthetic biomolecules, recombinant proteins, front-end capture, desalting, purification, SPE 75 and 150 micron Large scale purification, desalting, polishing of proteins and synthetic biomolecules Chromalite are offered in a particle size range from 5 micron up to 200 micron (larger particle size available in the standard range of products from Purolite) Chromalite are all spherical, synthetic resins made in uniform particle size range (U.C. < 1.5) 13

14 Chromalite particle size selection Particle size ( m) >200 Ion Exchange - Cation CGC10x6 CGC10x8 CGC50X2 CGC50X4 CGC50X8 CGC100X2 CGC100X4 CGC100X8 CGC200X2 CGC200X4 CGC200X8 Ion Exchange - Anion CGA10x6 CGA10x8 15SBG 15AD2Q CGA50X2 CGA50X4 CGA50X8 50SBM 50SBG CGA100X2 CGA100X4 CGA100X8 CGA200X2 CGA200X4 CGA200X8 Reversed Phase (RP) 5AD1 5AD2 5MN 10AD1 10AD2 10MN 15AD1 15AD2 15MN PCG1200F15 PCG1200F PCG900F PCG600F PCG1200M PCG900M PCG600M PCG1200CPlus PCG1200C PCG900C PCG600C Solid Phase Extraction (SPE) 70MN PCG1200MHEMA Macroporous (MP) type: AD, PCG, SBM - Obtained with porogens, DVB x-linking usually high. High porosity. Hypercrosslinked polystyrene adsorbents : MN - Hypercrosslinked adsorbents (MN) with extremely high surface area values (>1200 m 2 /g) and presence of nanopores. High surface areas optimal for adsorption of many organic substances (SPE). Non-porous (or gel-type): CGA/CGC, SBG - Obtained without porogen, with different DVB crosslinking. MDEA Highly porous methacrylate functionalized with diethylenamine. 14

15 Jetting: process for producing uniform particle size beads UC <1.2 Simple operation Higher yields Particle sizes from 150μm to 600μm Patented membrane technology 15

16 From analytical to preparative scale 5AD1, 5AD2, 10AD1, 10AD2, 15AD1, 15AD2, 15AD2Q 4.6 mm x 150 mm HPLC Column Analytical 4.6 mm x 250 mm HPLC Column Analytical 10.0 mm x 150 mm HPLC Column Preparative 10.0 mm x 250 mm HPLC Column Preparative 21.2 mm x 50 mm HPLC Column Preparative 21.2 mm x 100 mm HPLC Column Preparative 21.2 mm x 150 mm HPLC Column Preparative 21.2 mm x 250 mm HPLC Column Preparative 30.0 mm x 50 mm HPLC Column Preparative 30.0 mm x 100 mm HPLC Column Preparative 30.0 mm x 150 mm HPLC Column Preparative 30.0 mm x 250 mm HPLC Column Preparative 50.0 mm x 50 mm HPLC Column Preparative 50.0 mm x 250 mm HPLC Column Preparative All size for all demands 16

17 CONTROL OF POROSITY FOR EFFICIENT SEPARATIONS Source 15 RP SA: 423 m2/g PV: 0.62 ml/g Porosity: A PCG um SA: 730 m2/g PV = 1.42 ml/g Porosity: 1200 A Absence of nanopores in the region of 30A 17

18 CONTROL OF POROSITY FOR EFFICIENT SEPARATIONS PLRP-S 100 A (50 micron) SA: 507 m2/g PV: 1.05 ml/g Porosity: 300 A PCG1200F15 (15 micron) SA: 730 m2/g PV = 1.42 ml/g Porosity: 1200 A 18

19 Particle size control for efficient performance Source 15 RPC D50=14.7um, UC=1.00 PCG1200F15 D50= 15.2 um, UC=1.04 PLRP-S 300 A D50=10.3, UC= AD2 D50=10.7, UC=1.0 19

20 Optimal pressure stability Excellent Stability 20

21 Optimal resolution from analytical to preparative Insulin: 6.7 KDa CHP 55A 18 um (Mitsubishi) AMBERCHROM HPR10 10 micron (Dow) YMCbasic 15 micron (YMC Co.) Page 21 Excellent Scale-up purification 21

22 AD1 and AD2 materials optimal for RP separation of hydrophobic molecules Column length: 150 X4.6 mm Mobile Phase: 65/35 (ACN/KPi) Phosphate buffer 50 mm PO4 3- ph 3.2 Flow rate: 1 ml/min T: 21 C Detection: 254 ηm Injection volume: 10 μl 22

23 PLRP versus AD1 PLRP-S has different properties than AD1 material 23

24 PLRP versus AD1 Separation of peptides PLRP-S 10 um 300 A Column 4.6x150 mm Isocratic elution at 27% B А- 0,05% ТFA, В - 0,05% ТFA in 80% acetonitrile Flow rate- 0,5ml/min, pressure 1350 psi Resolution R= AD1 Column 4.6x150 mm Isocratic elution at 27% B А- 0,05% ТFA, В - 0,05% ТFA in 80% acetonitrile. Flow rate- 1ml/min, pressure 1515 psi Resolution R=1.09 octapeptide and its impurity (with 1 aminoacid missed) Good efficiency also with larger PS 24

25 PLRP versus AD2 Separation of peptides PLRP-S 10 um 300 A Column 4.6x150 mm Isocratic elution at 27% B А- 0,05% ТFA, В - 0,05% ТFA in 80% acetonitrile Flow rate- 0,5ml/min, pressure 1350 psi Resolution R= AD2 Column 4.6x150 mm Isocratic elution at 27% B А- 0,05% ТFA, В - 0,05% ТFA in 80% acetonitrile Flow rate- 1ml/min, pressure 1900 psi Resolution R=1.07 octapeptide and its impurity (with 1 aminoacid missed) Same performance of competitor 25

26 SILICA versus AD2 Separation of peptides Separation of hexa- (1 st peak) and octapeptide (2 nd ) Waters Symmetry 5 um silica C18 4.6x150 mm column Eluent 1 ml/min Linear gradient 10 40% acetonitrile in 0.05% TFA in water Retention factor R=2.9 10AD2 4.6x150 mm column Eluent 1 ml/min Linear gradient 10 40% acetonitrile in 0.05% TFA in water Retention factor R=2.8 Performances of 15 micron are same as 5 micron silica 26

27 PLRP versus AD2 Separation of benzene derivatives 1- phenol, 2- acetophenol, 3 nitrobenzene, 4 benzene, 5- toluene PLRP-S 300 A 10 um 4.6X150 mm column Isocratic Elution 60% acetonitrile Flow rate 1ml/min 15AD2 4.6x150 mm column Isocratic elution 60% acetonitrile Flow rate 1ml/min 27

28 Separation of sulfanilamide compounds Conditions: Column length: 150 x 4.6mm Mobile phase: 85/15 (Sodium Tetraborate 10H 2 O ph 9.30 / ACN) Flow rate: 1mL/min Detection: 254 nm Injection volume: 1 μl Page 28 28

29 Chromalite CGC and CGA Matrix: Gel polystyrene crosslinked with divinylbenzene (2, 4 and 7%) Application: For Fine Chemical and Pharmaceutical Column Separations ph Stability: Appearance CGC: Orange to dark brown spherical beads. Appearance CGA: Pale yellow to dark yellow spherical beads Expiry date from DOM: 5 years. Supplied we in H+ from (CGC) and Cl- from (CGA Product Functional group Total moisture % 90% in Range µm Volume capacity (eq/liter) Weight capacity (eq/kg) CGC50x2 Sulphonic acid min 5 min CGC50x4 Sulphonic acid min 5 min CGC50x8 Sulphonic acid min 5 min CGC100x2 Sulphonic acid min 5 min CGC100x4 Sulphonic acid min 5 min CGC100x8 Sulphonic acid min 5 min CGC200x2 Sulphonic acid min 5 min CGC200x4 Sulphonic acid min 5 min CGC200x8 Sulphonic acid min 5 min CGA50x2 Quaternary Ammonium min 4 min CGA50x4 Quaternary Ammonium min 4 min CGA50x8 Quaternary Ammonium min 3.5 min CGA100x2 Quaternary Ammonium min 4 min CGA100x4 Quaternary Ammonium min 4 min CGA100x8 Quaternary Ammonium min 3.5 min CGA200x2 Quaternary Ammonium min 4 min CGA200x4 Quaternary Ammonium min 4 min CGA200x8 Quaternary Ammonium min 3.5 min CGC: Gel Strong Acid Cation Chromatographic Resins CGA: Gel Strong Base Anion Exchange Chromatographic Resins 29

30 Chromalite CGC in acetate form Peptide TFA CGC/acetate Peptide Acetate Purolite can provide the ready to use CGC resins in acetate form RSF available Product Functional group Total moisture % 90% in Range µm Volume capacity (eq/liter) Weight capacity (eq/kg) CGC50x2 Sulphonic acid min 5 min CGC50x4 Sulphonic acid min 5 min CGC50x8 Sulphonic acid min 5 min CGC100x2 Sulphonic acid min 5 min CGC100x4 Sulphonic acid min 5 min CGC100x8 Sulphonic acid min 5 min CGC200x2 Sulphonic acid min 5 min CGC200x4 Sulphonic acid min 5 min CGC200x8 Sulphonic acid min 5 min Matrix: Gel polystyrene crosslinked with divinylbenzene (2, 4 and 7%) Application: For Fine Chemical and Pharmaceutical Column Separations ph Stability: Appearance CGC: Orange to dark brown spherical beads. Appearance CGA: Pale yellow to dark yellow spherical beads Expiry date from DOM: 5 years. Supplied we in H+ from (CGC) and Cl- from (CGA CGC: Gel Strong Acid Cation Chromatographic Resins CGA: Gel Strong Base Anion Exchange Chromatographic Resins 30

31 Resins for Solid Phase Peptide Synthesis Why Purolite for SPPS - world s premier resin technology manufacturer and innovation leader - Largest resin manufactures in Life Sciences - EU made resins: quality, regulatory, application specialists Official launch of resins for SPPS at Tides 2018 (Boston May 7-10, 2018) Request now your free sample for evaluation 31

32 Thank you Come and visit us at Purolite stand 80K10 25 th October Fred Ghanem

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