1228360-87-9Relevant academic research and scientific papers
A photocleavable masked nuclear-receptor ligand enables temporal control of C.elegans development
Judkins, Joshua C.,Mahanti, Parag,Hoffman, Jacob B.,Yim, Isaiah,Antebi, Adam,Schroeder, Frank C.
supporting information, p. 2110 - 2113 (2014/03/21)
The development and lifespan of C.elegans are controlled by the nuclear hormone receptor DAF-12, an important model for the vertebrate vitaminD and liverX receptors. As with its mammalian homologues, DAF-12 function is regulated by bile acid-like steroidal ligands; however, tools for investigating their biosynthesis and function invivo are lacking. A flexible synthesis for DAF-12 ligands and masked ligand derivatives that enable precise temporal control of DAF-12 function was developed. For ligand masking, photocleavable amides of 5-methoxy-N-methyl-2-nitroaniline (MMNA) were introduced. MMNA-masked ligands are bioavailable and after incorporation into the worm, brief UV irradiation can be used to trigger the expression of DAF-12 target genes and initiate development from dauer larvae into adults. The invivo release of DAF-12 ligands and other small-molecule signals by using photocleavable MMNA-masked ligands will enable functional studies with precise spatial and temporal resolution. Copyright
Second-generation synthesis of endogenous sperm-activating and attracting factor (SAAF) isolated from the ascidian Ciona intestinalis
Oishi, Tohru,Ootou, Kouichiro,Shibata, Hajime,Murata, Michio
supporting information; experimental part, p. 2600 - 2602 (2010/07/06)
Stereoselective synthesis of the chemoattractant sperm-activating and attracting factor (SAAF), isolated from the eggs of the ascidian Ciona intestinalis, was achieved via reductive 1,3-transposition of an allylic alcohol and the axial opening of an epoxide as key steps. This second-generation synthesis improved the total yield of SAAF over that of the first-generation synthesis and provided a key intermediate for synthesizing molecular probes of SAAF.
