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Ep 2787083 B1 (19) TZZ Z¥_T (11) EP 2 787 083 B1 (12) EUROPEAN PATENT SPECIFICATION (45) Date of publication and mention (51) Int Cl.: of the grant of the patent: C12P 21/04 (2006.01) 14.06.2017 Bulletin 2017/24 (21) Application number: 14164176.1 (22) Date of filing: 09.11.2010 (54) EFFICIENT PRODUCTION OF PEPTIDES EFFIZIENTE HERSTELLUNG VON PEPTIDEN PRODUCTION EFFICACE DE PEPTIDES (84) Designated Contracting States: • NEMKOV, Travis AL AT BE BG CH CY CZ DE DK EE ES FI FR GB Boulder, CO 80309 (US) GR HR HU IE IS IT LI LT LU LV MC MK MT NL NO • HIESTER, Brian PL PT RO RS SE SI SK SM TR Boulder, CO 80305 (US) • BOUX, Leslie (30) Priority: 09.11.2009 US 259367 P Boulder, CO 80304 (US) • PLAM, Mikhail (43) Date of publication of application: Boulder, CO 80304 (US) 08.10.2014 Bulletin 2014/41 (74) Representative: Russell, Tim et al (62) Document number(s) of the earlier application(s) in Venner Shipley LLP accordance with Art. 76 EPC: 200 Aldersgate 10829265.7 / 2 499 255 London EC1A 4HD (GB) (73) Proprietors: (56) References cited: • The Regents of the University of Colorado, a body WO-A2-2009/066320 US-A1- 2003 219 854 corporate US-A1- 2007 128 622 US-A1- 2008 096 245 Denver, CO 80203 (US) • AmideBio LLC • UHLEN M ET AL: "Fusion proteins in Boulder, CO 80304 (US) biotechnology", CURRENT OPINION IN BIOTECHNOLOGY, LONDON, GB, vol. 3, no. 4, 1 (72) Inventors: August 1992 (1992-08-01), pages 363-369, • STOWELL, Michael XP023601584, ISSN: 0958-1669, DOI: Boulder, CO 80309 (US) 10.1016/0958-1669(92)90164-E [retrieved on • CARUTHERS, Jonathan 1992-08-01] Boulder, CO 80309 (US) Note: Within nine months of the publication of the mention of the grant of the European patent in the European Patent Bulletin, any person may give notice to the European Patent Office of opposition to that patent, in accordance with the Implementing Regulations. Notice of opposition shall not be deemed to have been filed until the opposition fee has been paid. (Art. 99(1) European Patent Convention). EP 2 787 083 B1 Printed by Jouve, 75001 PARIS (FR) EP 2 787 083 B1 Description CROSS-REFERENCE TO RELATED APPLICATIONS 5 [0001] This application claims priority from U.S. Provisional Application 61/259,367, filed November 9, 2009. FIELD OF THE INVENTION [0002] The presentinvention relates to processes for the productionof peptides, andthe peptides producedaccordingly. 10 Peptides produced according to the invention may be produced more efficiently than peptides produced according to prior art processes. The production process of the invention may lead to advantages in yield, purity, and/or price. Methods of marketing peptides are also disclosed. BACKGROUND OF THE INVENTION 15 [0003] Peptides are becoming increasingly useful in basic research and clinical practice. Interest in peptides can be attributed to their role as mediators in many biological pathways and to their unique intrinsic properties. For example, many peptides have high specificity for their target with low non-specific binding to molecules that are not targeted, thus minimizing drug-drug interactions, and many peptides show low accumulation in tissues over time, thus reducing side 20 effects. Moreover, peptides are often broken down in vivo to their constituent amino acids, thus reducing the risk of complications due to toxic metabolic intermediates. [0004] Peptide market values are generally grouped within five broad categories in the life sciences field: cytokines, enzymes, hormones, monoclonal antibodies, and vaccines. According to a 2008 Frost & Sullivan market research report, these broad categories can be further subdivided in the United States into vaccines (34%), monoclonal antibodies (30%), 25 recombinant hormones and proteins (10%), gene therapy (6%), cell therapy (4%), antisense (3%), interferons (3%), interleukins (2%), growth factors (1%), and others (7%). Each of these categories is undergoing high growth rates. For example, from 2004 to 2007, the monoclonal antibody market alone almost doubled its revenue from $6.3 billion to $12.6 billion. In addition, several new products, including Bydureon® (exenatide LAR for diabetes; Amylin/Eli Lilly), Extavia® (interferon beta-1b for multiple sclerosis; Novartis), and Simponi™ (golimumab for rheumatoid and psoriatic arthritis; 30 Centocor) have been approved recently by the FDA. [0005] Moreover, peptide markets are likely to continue to grow. For example, of 633 drugs in development in 2008, nearly half were peptides. Analysts estimate an eight per cent compound annual growth rate over the next half-decade resulting in a potential $20 billion in earnings for the year 2013, representing nearly fifteen per cent of the forecast total earnings for the biopharmaceuticals market. Additional opportunities exist for peptides as reagents in basic research 35 and diagnostic platforms. [0006] While advances in the field of peptide science have led to impressive commercial growth, several barriers remain to be overcome. For example, peptides tend to have delivery and stability problems compared to traditional small molecule therapeutics. Attempts to address these problems have involved oral, nasal, and pulmonary delivery. However, these attempts often require higher doses of the peptides or yield unfavorable pharmacokinetic profiles. 40 [0007] One of the biggest barriers to increased use of peptides is the cost of the peptides themselves, which is generally significantly higher than the cost of producing small molecule therapeutics. For instance, Nutropin AQ®, a form of recombinant human growth hormone manufactured by Genentech and administered to patients with growth defects during adolescence, costs $30,000 annually. High prices are an even bigger barrier to obtaining peptides when the peptideis used for research purposes.For example, β-amyloid(1-42) peptide is a research peptide with strong implications 45 in the onset of Alzheimer’s disease. A survey of prices from various peptide manufacturers finds the price of research- grade β-amyloid (1-42) ranging from $225/mg (21 st Century Biochemicals) to $1,490/mg (Sigma-Aldrich), with the typical price at $300-$320/mg (AnaSpec, California Peptide, Innovagen, rPeptide) (estimated 2009 prices as obtained from catalogs). [0008] Due to the importance of peptides and their high price, there is a persistent and long-felt yet unfulfilled need 50 for lowering the cost of peptides. The industrial and medical use of peptides has created a need for an improved means of production and purification, where the improvement may be in efficiency, price, and/or quality of product. Accordingly, the present invention is directed to processes for the production of peptides, and the peptides produced. Methods of marketing peptides are also disclosed. 55 SUMMARY OF THE INVENTION [0009] In various embodiments, the invention is directed to a method for producing a target peptide. According to the method of the invention, a fusion peptide is produced comprising an affinity tag, a cleavable tag, and the target peptide, 2 EP 2 787 083 B1 followed by binding of the fusion peptide to an affinity material, cleaving the fusion peptide with N-chlorosuccinimide to release the target peptide; and removing the target peptide from the affinity material. In general, following binding of the fusion peptide to an affinity material, the affinity material is washed to remove unbound material. Moreover, following removal of the target peptide from the affinity material, the target peptide may be further modified or packaged for 5 distribution. [0010] The target peptide is not limited, and may include a wide variety of peptides. For example, in various embod- iments, the target peptide is selected from the group consisting of amyloid beta, calcitonin, enfuvirtide, epoetin, epoetin delta, erythropoietin, exenatide, factor VIII, factor X, glucocerebrosidase, glucagon-like peptide-1 (GLP-1), granulocyte- colony stimulating factor (G-CSF), human growth hormone (hGH), insulin, insulin A, insulin B, insulin-like growth factor 10 1 (IGF-1), interferon, liraglutide, somatostatin, teriparatide, and tissue plasminogen activator (TPA). In various embod- iments, the target peptide is selected from amyloid beta, enfuvirtide, exenatide, insulin, and teriparatide. [0011] The fusion peptide may be produced in a variety of methods. In one embodiment, the fusion peptide is produced in a bacterial expression system, such as an E. coli expression system. In alternate embodiments, the expression system is a yeast expression system or a mammalian expression system. 15 [0012] In various embodiments, the fusion peptide according to the invention further comprises an inclusion-body directing peptide. In such embodiments, prior to the binding of the fusion peptide to the affinity material, the fusion peptide may be isolated from the expression system by separation of inclusion bodies from the remainder of the cell in the expression system. Following initial isolation, the fusion peptide may be solubilized to allow further handling. In various embodiments, the inclusion-body directing peptide is selected from the group consisting of inclusion-body directing 20 peptide is a ketosteroid isomerase, an inclusion-body directing functional fragment of a ketosteroid isomerase, an in- clusion-body directing functional homolog of a ketosteroid isomerase, a BRCA2 peptide, an inclusion-body directing functional fragment of BRCA2, or an inclusion-body directing functional homolog of BRCA2. [0013] In various embodiments, the affinity tag is selected from the group consisting of poly-histidine, poly-lysine,
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