Investigation of Parameters that Affect Resin Swelling in Green Solvents

被引:12
作者
Amadi-Kamalu, Chidi [1 ]
Clarke, Holly [1 ]
McRobie, Matthew [1 ]
Mortimer, James [1 ]
North, Michael [1 ]
Ran, Yanrui [1 ]
Routledge, Anne [1 ]
Sibbald, Dani [1 ]
Tickias, Matthew [1 ]
Tse, Kai [1 ]
Willway, Helen [1 ]
机构
[1] Univ York, Dept Chem, York YO10 5DD, N Yorkshire, England
关键词
polystyrene; solvent; swelling; ChemMatrix; peptide; PHASE PEPTIDE-SYNTHESIS; PERSPECTIVE;
D O I
10.1002/open.202000030
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
The influence of various physical and chemical factors on the swelling of polystyrene and PEG based resins in greener organic solvents has been systematically investigated. In general, chemical factors: the nature of the functionality/linker and the degree of loading were found to have a far larger influence on the swelling of the resins than physical parameters such as bead size. The results are interpreted in terms of Hansen solubility parameters for the solvents and there is evidence that some solvents interact with the polymeric core of a resin whilst others interact with the functionality. The results are extended to a study of the changes in resin swelling observed during both deprotection and chain elongation reactions during solid phase peptide synthesis.
引用
收藏
页码:431 / 441
页数:11
相关论文
共 36 条
[1]   Updating and further expanding GSK's solvent sustainability guide [J].
Alder, Catherine M. ;
Hayler, John D. ;
Henderson, Richard K. ;
Redman, Aniko M. ;
Shukla, Lena ;
Shuster, Leanna E. ;
Sneddon, Helen F. .
GREEN CHEMISTRY, 2016, 18 (13) :3879-3890
[2]  
[Anonymous], HSPIP SOFTWARE
[3]   Selection of a Greener Set of Solvents Evenly Spread in the Hansen Space by Space-Filling Design [J].
Benazzouz, Adrien ;
Moity, Laurianne ;
Pierlot, Christel ;
Sergent, Michelle ;
Molinier, Valerie ;
Aubry, Jean-Marie .
INDUSTRIAL & ENGINEERING CHEMISTRY RESEARCH, 2013, 52 (47) :16585-16597
[4]   A rink-amide soluble support: high purity conotoxins and other peptides accessed with minimal reagents [J].
Bisht, Babita ;
Naganna, Nimmashetti ;
Madhavan, Nandita .
ORGANIC & BIOMOLECULAR CHEMISTRY, 2019, 17 (30) :7238-7246
[5]   Resins with Identical Specifications Are Not Identical. Identifying a Useful Solid-Phase Resin [J].
Bouillon, Isabelle ;
Soural, Miroslav ;
Miller, Marvin J. ;
Krchnak, Viktor .
JOURNAL OF COMBINATORIAL CHEMISTRY, 2009, 11 (02) :213-215
[6]   Key Green Chemistry research areas from a pharmaceutical manufacturers' perspective revisited [J].
Bryan, Marian C. ;
Dunn, Peter J. ;
Entwistle, David ;
Gallou, Fabrice ;
Koenig, Stefan G. ;
Hayler, John D. ;
Hickey, Matthew R. ;
Hughes, Shaun ;
Kopach, Michael E. ;
Moine, Gerard ;
Richardson, Paul ;
Roschangar, Frank ;
Steven, Alan ;
Weiberth, Franz J. .
GREEN CHEMISTRY, 2018, 20 (22) :5082-5103
[7]   What is a green solvent?: A comprehensive framework for the environmental assessment of solvents [J].
Capello, Christian ;
Fischer, Ulrich ;
Hungerbuehler, Konrad .
GREEN CHEMISTRY, 2007, 9 (09) :927-934
[8]   Perspective on solvent use in the pharmaceutical industry [J].
Constable, David J. C. ;
Jimenez-Gonzalez, Conchita ;
Henderson, Richard K. .
ORGANIC PROCESS RESEARCH & DEVELOPMENT, 2007, 11 (01) :133-137
[9]  
European Chemical Agency, LIST SUBST INCL ANN
[10]   Green Solvent Mixtures for Solid-Phase Peptide Synthesis: A Dimethylformamide-Free Highly Efficient Synthesis of Pharmaceutical-Grade Peptides [J].
Ferrazzano, Lucia ;
Corbisiero, Dario ;
Martelli, Giulia ;
Tolomelli, Alessandra ;
Viola, Angelo ;
Ricci, Antonio ;
Cabri, Walter .
ACS SUSTAINABLE CHEMISTRY & ENGINEERING, 2019, 7 (15) :12867-12877