Acid-Mediated Prevention of Aspartimide Formation in Solid Phase Peptide Synthesis
Aspartimide formation is one of the major obstacles that impedes the solid phase synthesis of large peptides and proteins. Until now, no cost-effective strategy to suppress this side reaction has been developed. Here it is demonstrated that addition of small amounts of organic acids to the standard...
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| Veröffentlicht in: | Organic letters 2012-10, Vol.14 (20), p.5218-5221 |
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| container_title | Organic letters |
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| creator | Michels, Tillmann Dölling, Rudolf Haberkorn, Uwe Mier, Walter |
| description | Aspartimide formation is one of the major obstacles that impedes the solid phase synthesis of large peptides and proteins. Until now, no cost-effective strategy to suppress this side reaction has been developed. Here it is demonstrated that addition of small amounts of organic acids to the standard Fmoc cleavage agent piperidine efficiently prevents formation of aspartimide side products. This effect is shown to be virtually independent of the acid strength. |
| doi_str_mv | 10.1021/ol3007925 |
| format | Article |
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| identifier | ISSN: 1523-7060 |
| ispartof | Organic letters, 2012-10, Vol.14 (20), p.5218-5221 |
| issn | 1523-7060 1523-7052 |
| language | eng |
| recordid | cdi_proquest_miscellaneous_1237085771 |
| source | ACS Publications; MEDLINE |
| subjects | Acids - chemistry Aspartic Acid - analogs & derivatives Aspartic Acid - chemical synthesis Hydrogen-Ion Concentration Molecular Structure Solid-Phase Synthesis Techniques |
| title | Acid-Mediated Prevention of Aspartimide Formation in Solid Phase Peptide Synthesis |
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