Advancing Peptide Synthesis: Liquid-Phase Assembly of Tirzepatide’s C-Terminus (30–39) via Crystalline Pentamer Building Blocks
Traditional solid-phase peptide synthesis (SPPS) is limited in its suitability for high-volume peptide/protein manufacturing applications due to its reliance on specialized equipment, high process mass intensity (PMI), and the use of environmentally concerning reagents. To address these limitations, a fully liquid-phase peptide synthesis (LPPS) has been developed and applied to the synthesis of a tirzepatide (30–39) fragment intermediate. This method leverages Fmoc- and Cbz-protecting group strategies to generate two high-purity crystalline pentamers entirely without solid-phase techniques. Subsequent solution-phase assembly of the pentamers yields the desired decapeptide. This green, efficient, and practical route offers a more economical and environmentally favorable alternative to SPPS, delivering a fragment intermediate of superior quality. Additionally, tirzepatide (30–39) decapeptide is a potential common intermediate for numerous other incretin peptides using hybrid SPPS/LPPS methodologies.
Authors
- Michael E. Kopach (ORCID: https://orcid.org/0000-0002-3590-702X)
- Kevin D. Seibert (ORCID: https://orcid.org/0000-0003-0626-0033)
- Mark R. Berglund
- Jing Teng (ORCID: https://orcid.org/0000-0001-5099-4670)
- Paridhi Agrawal (ORCID: https://orcid.org/0000-0002-8290-3275)
- Emily Murzinski Valco
Institutions
- Eli Lilly (United States) (US)
Publication Details
- Journal
- Organic Process Research & Development
- Published
- 2025-10-23
- DOI
- https://doi.org/10.1021/acs.oprd.5c00304
- Citations
- 1
- Primary Topic
- Chemical Synthesis and Analysis
- Type
- article
- Field-Weighted Citation Impact
- 0.81