Synthesis of Caged HMG-CoA Reductase Substrates for the Elucidation of Cellular Pathways
The synthesis of photocaged substrates of the biologically important enzyme HMG-CoA reductase is reported. HMG-CoA bearing a <i>p</i>-hydroxyphenacyl (pHP) photocage moiety was synthesized in an overall yield of 14% over seven steps in addition to caged forms of mevalonate and mevaldehyde. The absorption maximum and quantum yield for the decaging of the photocaged compounds are dependent on pH with a λ<sub>max</sub> of 330 nm and a ϕ of 5%, respectively, at pH 9.1 but a λ<sub>max</sub> of 290 nm and a ϕ of 16%, respectively, at pH 6.7.
Authors
- Paul Helquist (ORCID: https://orcid.org/0000-0003-4380-9566)
- Mijoon Lee (ORCID: https://orcid.org/0000-0001-7432-0427)
- Olaf Wiest (ORCID: https://orcid.org/0000-0001-9316-7720)
- Cynthia V. Stauffacher (ORCID: https://orcid.org/0000-0002-3081-6903)
- Ryan P. O’Connell (ORCID: https://orcid.org/0000-0003-3808-4281)
- G. Ferraudi (ORCID: https://orcid.org/0000-0003-2840-5520)
- Nicholas J. Dolphin
Institutions
- University of Notre Dame (US)
- Purdue University West Lafayette (US)
Publication Details
- Journal
- The Journal of Organic Chemistry
- Published
- 2024-12-06
- DOI
- https://doi.org/10.1021/acs.joc.4c02403
- Primary Topic
- Photochromic and Fluorescence Chemistry
- Type
- article
- Field-Weighted Citation Impact
- 0.00
Funders
- National Institutes of Health
- National Institute of General Medical Sciences