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

Stolze, Sara C., Meltzer, Michael, Ehrmann, Michael 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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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: 04 Jun 2017 06:10

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