Phenylglycine racemization in Fmoc-based solid-phase peptide synthesis: stereochemical stability is achieved by choice of reaction conditions
Phenylglycine-containing peptides have broad applications in medicinal chemistry, but their synthetic accessibility is complicated by the risk of epimerization during solid-phase peptide synthesis (SPPS). Phenylglycine is therefore often considered a troublesome residue. This work studies the extent...
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| Main Authors: | , , , |
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| Format: | Article (Journal) |
| Language: | English |
| Published: |
21 April 2017
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| In: |
Tetrahedron letters
Year: 2017, Volume: 58, Issue: 24, Pages: 2325-2329 |
| ISSN: | 1873-3581 |
| DOI: | 10.1016/j.tetlet.2017.04.047 |
| Online Access: | Verlag, Volltext: http://dx.doi.org/10.1016/j.tetlet.2017.04.047 Verlag, Volltext: http://www.sciencedirect.com/science/article/pii/S0040403917304872 
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| Author Notes: | Chen Liang, Mira A.M. Behnam, Tom R. Sundermann, Christian D. Klein |
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| 520 | |a Phenylglycine-containing peptides have broad applications in medicinal chemistry, but their synthetic accessibility is complicated by the risk of epimerization during solid-phase peptide synthesis (SPPS). Phenylglycine is therefore often considered a troublesome residue. This work studies the extent of Phg racemization under different Fmoc-SPPS reaction conditions. It is shown that the base-catalyzed coupling of Fmoc-Phg is the critical step for racemization. However, racemization can be reduced to a negligible level if DEPBT or COMU combined with TMP or DMP are employed during this step. Resin-bound peptides are remarkably resistant against epimerization during extended incubation under basic conditions and the free peptides were stable in buffer solutions used for biological assays. | ||
| 650 | 4 | |a Epimerization | |
| 650 | 4 | |a Peptides | |
| 650 | 4 | |a Phenylglycine | |
| 650 | 4 | |a Racemization | |
| 650 | 4 | |a Solid-phase peptide synthesis | |
| 650 | 4 | |a Stability | |
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