Challenges in Industrial Production of Peptides. Dr. Daniel Bourgin Director of Sales & BD LCM-TIDES, Lonza Ltd. Basel, Switzerland
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1 Challenges in Industrial Production of Peptides Dr. Daniel Bourgin Director of Sales & BD LCM-TIDES, Lonza Ltd. Basel, Switzerland
2 Agenda Market Trend Technology Trend Challenges Lonza s Technology portfolio Strategy of Synthesis Economy slide 2
3 Market Trend Peptides Total global market potential API level (in-house and CMO) = 1bn USD Market growth = 10 15% p.a. Launched Peptides = in Clinical Phase >200 in Pre-Clinical Emerging areas: Cancer, HIV, Cardiovascular, CNS and Metabolic disorders Generic peptides 2005 substantial investment (CHF 24 Mio) in Peptides Number of candidates Worldwide Peptide Pipeline (synthetic) pre-clinical phase I Source: Market Research phase II phase III launched slide 3
4 slide 4 Technology Trend Market faces the challenge to produce peptides in kilograms and >100kg (industrial conditions) Increasing importance of long peptides 3 Technologies available for production of Peptides Solid-Phase Synthesis Liquid-Phase Synthesis Recombinant Technology Proven scale ability of peptide chemistry up to 1000 l reactors The supplier-customer relationship is becoming more complex requiring an intensive collaboration throughout the whole life cycle of the product
5 slide 5 Some characteristic Peptides Product Length Product characteristics Estimated API Demand Bivalirudin 20 1 unnatural amino acid > 100 kg Eptifibatide (Integrilin) Enfuvirtide (T-20), Fuzeon 7 Peptide amide 100 kg Cyclic peptide, S-S bridge 2 unnatural building blocks 36 Long peptide, peptide amide >500 kg N-Terminus modified ( > 1 to?) Calcitonins 32 All natural amino acids, chemical and recombinant routes >100kg Teriparatide 34 Long peptide, hormone regulator (recombinant) Zadaxin 28 Long peptide, chemical synthesis > 100 kg Abarelix 10 6 unnatural amino acids, Peptide amide N-Terminus modified Symlin 39 All natural amino acids, recomb & chem. synthesis 10 kg >100kg
6 slide 6 Challenges Right strategy of synthesis applicable on all scales Quality of the peptide, single impurity profile, scale-up issues Regulation, ICH guidelines small molecules, status in the lifecycle Economy, cost of goods Down stream processing and isolation Logistic
7 slide 7 Scale-up effect in Solid-Phase synthesis of a long peptide Crude peptide, Qualification laboratory sample: Crude peptide, Launch plant material:
8 slide 8 LONZA, Exclusive Synthesis Production Concept Recombinant Technology Solid Phase Synthesis Biotec pilot plant, Visp Liquid Phase Synthesis Solid Phase Peptide Synthesizer, Visp
9 Strategy of Synthesis-Liquid Phase Pro Method of choice for production of short peptides BOC, CbZ strategy, less expensive raw materials Impurity profile, high chance to be easy Unlimited capacity Con Limitation in number of AA to be combined Convergent Synthesis Number of unit operations Long cycle time Yield slide 9
10 Strategy of Synthesis-Solid Phase Pro Merrifield, Fmoc Strategy, orthogonal protection groups opened the door to the rapid synthesis of long peptides Physical-chemical properties of the growing peptide can be controlled Process is automatable and scaleable No isolation of intermediates Short production cycles Con (Expensive raw materials) Might generate a complex impurity profile slide 10
11 slide 11 Convergent SPPS - Hybridal Technology H OH H Repeat n times H Final deprotection OH
12 Solid Phase Synthesis of long peptides Issues: Insertion, deletion, double-hits With increasing peptide length, chain aggregation, leads to truncated peptides, purification, yield Synthesis of peptides with residuals for commercial production are possible (GLP-1 analogs) slide 12
13 Solid Phase Synthesis slide 13
14 slide 14 Buffer A Buffer B Peptide crude dissolution DSP: Purification 0.45 m filtration 0.45 m filtration 0.45 m filtration HPLC 60 cm Column DCM UV Ok-Pool Selector Side fractions DCM To recycle HPLC 60 cm Column Concentration 0.2 m Filtration Lyophilization DCM
15 Lyophilisation slide 15
16 slide 16 Logistical Aspects (Example:) An average 9 mer peptide in conjunction with customers requirements (annual demand of peptide API): Raw Material Peptide / API vs. raw materials Requirements 20 kg 100 kg 200 kg 500 kg Amino acid 0.4 to 2.0 to 4.0 to 10.0 to TCTU 0.3 to 1.3 to 2.6 to 6.5 to Piperidine 6.5 to 33 to 65 to 163 to NMP 100 to 500 to 1000 to 2500 to DCM 80 to 400 to 800 to 2000 to ACN 35 to 175 to 350 to 875 to USP water 300 to 1500 to 3000 to 7500 to annual demand in metric tons Strategic (worldwide) sourcing activities, raw material supply in rail-tank-cars, tank-farms, no open handling, recycling systems, adequate warehousing.
17 slide 17 Strategy of Synthesis: Recombinant Peptide Production Production organism Product localization as concatemer Makes sense for Has limited sense for Advantage 1. E. coli intracellular Hydrophilic peptides, no secondary or tertiary structure Strongly hydrophobic peptides (Inclusion bodies) High product concentrations 5 10 g/l fermentation br. 2. E. coli periplasmic Peptides/ proteins with sec./ tert. structure (S-S) Peptides/ proteins without sec./ tert. structure (S-S) Use of secretion to generate biological active conformation; 3. Pichia angusta fermentation medium Hydrophilic & slightly hydroph. peptide/proteins +/- sec / tert.str. Strong hydrophobic peptides/proteins Secretion of right confirmation, less unit operations
18 KUP 15 Fermentor 15m3 slide 18
19 slide 19 Example of a tricky Peptide Cationic peptide- 13 mer H-AA 1 -AA 2 -Arg 3 -AA 4 -AA 5 -AA 6 -AA 7 -AA 8 -AA 9 -AA 10 -Arg 11 -AA 112 -A 13 -NH 2
20 slide 20 Cationic Peptide Synthesis Expressed peptide H-AA 1 -AA 2 -Arg 3 -AA 4 -AA 5 -AA 6 -AA 7 -AA 8 -AA 9 -AA 10 -Arg 11 -AA 12 -AA 13 -OH Protection with DiBOC Yield 98% Purity 97% Chemical Amidation with NH 3 H-AA 1 -AA 2 -Arg 3 -AA 4 -AA 5 -AA 6 -AA 7 -AA 8 -AA 9 -AA 10 -Arg 11 -AA 12 -AA 13 -NH 2
21 slide 21 Cationic Peptide Synthesis Cl CTC (0.4 mmol/g) Fmoc-Arg(Pbf) 1) Fmoc-Arg(Pbf)-OH (1.5eq), DIEA 2) MeOH CTC lenghtening 1) Fmoc-AA-OH, HBTU, DIEA 2) Ac 2 O/pyridine/DMF if require 3) 20% piperidine H-AA 1 -AA 2 -Arg 3 -AA 4 -AA 5 -AA 6 -AA 7 -AA 8 -AA 9 -AA 10- Arg(Pbf) CTC cleavage 2% TFA/DCM H-AA 12 (Boc)-AA 13 (Boc)-NH 2 HBTU, DIEA deprotection 95% TFA/H 2 O/anisole H-AA 1 -AA 2 -Arg 3 -AA 4 -AA 5 -AA 6 -AA 7 -AA 8 -AA 9 -AA 10 -Arg 11 -AA 12 -AA 13 -NH 2 Purification yield 80%
22 Results Cationic Peptide Semi-synthetic route discontinued Switch to alternative solid phase route in Phase II Economy comparable with the bio-route at large scale slide 22
23 slide 23 Economical aspects-production Cost Raw materials Production Determining factor Solid Phase Route 30-40% of overall costs 60 % including purification& isolation Raw material situation, waste stream, atom economy Recombinant 5% 95 % including DSP-1, purification and isolation Unit operations, high development cost including scale-up Common bottleneck HPLC-purification & Isolation
24 Conclusion: Strategy of Synthesis: Technology Combination Chart Entry Solid Phase Liquid Phase Recombinant Solid Phase mer <20 mer fragments Peptides containing modified/nonmodified amino acids Scale: gram -MT Fragment condensation Peptides containing modified/non-modified amino acids Scale: gram-mt Liquid Phase Recombinant Fragments <10 mer Fragment condensation All types of AA Scale: gram-mt Fragment condensation Scale: >100kg-MT >10 mer-proteins Complex All natural AA Scale: >100kg-MT slide 24
25 slide 25 THANK YOU FOR YOUR ATTENTION! We invite you to our booth 9F12, Hall 9
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