Chemistry:PyBOP
From HandWiki
PyBOP (benzotriazol-1-yloxytripyrrolidinophosphonium hexafluorophosphate) is a reagent used to prepare amides from carboxylic acids and amines in the context of peptide synthesis.[1] It can be prepared from 1-hydroxybenzotriazole and a chlorophosphonium reagent under basic conditions.[2] It is a substitute for the BOP reagent that avoids the formation of the carcinogenic waste product HMPA.[3] Thermal hazard analysis by differential scanning calorimetry (DSC) shows PyBOP is potentially explosive.[4]
See also
- BOP reagent
- DEPBT, a related reagent that contains no phosphorus-nitrogen bonds
- HATU
- HBTU
References
- ↑ Mansour, Tarek S.; Bardhan, Sujata; Wan, Zhao-Kui (2010). "Phosphonium- and Benzotriazolyloxy-Mediated Bond-Forming Reactions and Their Synthetic Applications" (in en). Synlett 2010 (8): 1143–1169. doi:10.1055/s-0029-1219820. ISSN 0936-5214. http://www.thieme-connect.de/DOI/DOI?10.1055/s-0029-1219820.
- ↑ Hoffmann, Frank; Jäger, Lothar; Griehl, Carola (2003). "Synthesis and Chemical Constitution of Diphenoxyphosphoryl Derivatives and Phosphonium Salts as Coupling Reagents for Peptide Segment Condensation" (in en). Phosphorus, Sulfur, and Silicon and the Related Elements 178 (2): 299–309. doi:10.1080/10426500307942. ISSN 1042-6507. https://www.tandfonline.com/doi/full/10.1080/10426500307942.
- ↑ Coste, J.; Le-Nguyen, D.; Castro, B. (1990). "PyBOP®: A new peptide coupling reagent devoid of toxic by-product". Tetrahedron Letters 31 (2): 205. doi:10.1016/S0040-4039(00)94371-5.
- ↑ Sperry, Jeffrey B.; Minteer, Christopher J.; Tao, JingYa; Johnson, Rebecca; Duzguner, Remzi; Hawksworth, Michael; Oke, Samantha; Richardson, Paul F. et al. (2018-09-21). "Thermal Stability Assessment of Peptide Coupling Reagents Commonly Used in Pharmaceutical Manufacturing" (in en). Organic Process Research & Development 22 (9): 1262–1275. doi:10.1021/acs.oprd.8b00193. ISSN 1083-6160. https://pubs.acs.org/doi/10.1021/acs.oprd.8b00193.
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