Development of a solid-phase approach to the natural product class of Ahp-containing cyclodepsipeptides

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

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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:	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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