Enabling routine fluorous capping in solid phase peptide synthesis |
| |
| Institution: | 1. Department of Chemistry, Tufts University Medford, MA 02155, USA;2. Tufts-New England Medical Center, Boston, MA 02110, USA;1. Department of Chemistry, Chemistry Research Laboratory, University of Oxford, 12 Mansfield Road, Oxford OX1 3TA, United Kingdom;2. Structural Genomics Consortium, University of Oxford, Old Road Campus Roosvelt Drive, Headington OX3 7DQ, United Kingdom;1. Center for Analysis and Synthesis, Lund University, Lund, Sweden;2. Glactone Pharma AB, Helsingborg, Sweden;3. Division of Urological Cancers, Department of Translational Medicine, Lund University, Malmö, Sweden;1. Pacific Institute of Bioorganic Chemistry, Far East Branch of the Russian Academy of Sciences, Prospect 100 let Vladivostoku, 159, Vladivostok 690022, Russian Federation;2. Far Eastern Federal University, Sukhanova Road 8, Vladivostok 690000, Russian Federation;1. School of Chemistry, National University of Ireland, Galway, Galway, Ireland;2. School of Chemistry, University of Birmingham, Edgbaston B15 2TT, United Kingdom;3. Faculty of Medicine and Health Science, University of Nottingham, Queens Medical Centre, Nottingham NG7 2RD, United Kingdom;4. National Centre for Macromolecular Hydrodynamics, University of Nottingham, Nottingham LE12 5RD, United Kingdom;1. School of Life Science and Technology, State Key Laboratory of Urban Water Resource and Environment, Harbin Institute of Technology, 92 West Dazhi Street, Harbin 150001, China;2. State Key Laboratory of Medicinal Chemical Biology, Nankai University, Tianjin, China;1. University of North Texas, Department of Physics and Advanced Materials & Manufacturing Institute, 1155 Union Circle, Denton, TX 76203, USA;2. Military University of Technology, Institute of Optoelectronics, 2 Kaliskiego Str., 00-908 Warsaw, Poland;3. Skolkovo Institute of Science and Technology, 3 Nobel St., Moscow 143026, Russia |
| |
| Abstract: | We describe here the use of polyfluorinated trivalent iodonium salts as efficient and robust capping reagents during solid phase peptide synthesis using either t-Boc or Fmoc chemistry. Standard protocols established for solid phase peptide synthesis can be utilized without any change in solvent or reagent conditions. The capping reaction was carried out at sites where amino acid coupling steps failed. At the termination of the synthesis, the crude peptide mixture obtained from release of materials from the resin, is either simply centrifuged in aqueous solution to yield pure peptide, or purified by passage through fluorous silica gel in solvents with high water content. We envision that the chemistry and reagents described here will find wide use in peptide and protein chemistry, and also in combinatorial library synthesis where terminal amines are coupled to reaction partners. |
| |
| Keywords: | |
| 本文献已被 ScienceDirect 等数据库收录！ |
|
