Stolze, Sara C., Meltzer, Michael, Ehrmann, Michael  ORCID: https://orcid.org/0000-0002-1927-260X and Kaiser, Markus
2012.
Development of a solid-phase approach to the natural product class of Ahp-containing cyclodepsipeptides.
European Journal of Organic Chemistry
2012
(8)
, pp. 1616-1625.
10.1002/ejoc.201101757
|
Abstract
The 3-amino-6-hydroxy-2-piperidone (Ahp) containing cyclodepsipeptides are an interesting class of natural products that inhibit S1 (trypsin and chymotrypsin-like) serine protease in a reversible, noncovalent manner, turning them into potential chemical tools for protease research. Their systematic use in chemical biology is however hampered by their tedious solution-phase chemical synthesis. To overcome this limitation, we report a solid-phase approach to Ahp cyclodepsipeptides that is based on the use of a maskedglutamic aldehyde moiety as a general Ahp precursor molecule. As a proof-of-concept, we therefore recently reported the solid-phase synthesis of Symplocamide A. Here, we want to give a full account on the development and application of the masked glutamic aldehyde moiety as well as the optimization of the solid-phase synthesis, which allowed the successful synthesis of the natural product Symplocamide A.
| Item Type: | Article |
|---|---|
| Date Type: | Publication |
| Status: | Published |
| Schools: | Schools > Biosciences |
| Subjects: | Q Science > QD Chemistry |
| Uncontrolled Keywords: | Solid-phase synthesis; Natural products; Peptides; Masked glutamic aldehyde |
| Publisher: | Wiley |
| ISSN: | 1434-193X |
| Last Modified: | 25 Oct 2022 09:02 |
| URI: | https://orca.cardiff.ac.uk/id/eprint/56925 |
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