Literature DB >> 19225674

Synthesis and biological activity of the (25R)-cholesten-26-oic acids--ligands for the hormonal receptor DAF-12 in Caenorhabditis elegans.

René Martin1, Arndt W Schmidt, Gabriele Theumer, Tilo Krause, Eugeni V Entchev, Teymuras V Kurzchalia, Hans-Joachim Knölker.   

Abstract

We describe the stereoselective transformation of diosgenin (4a) to (25R)-Delta(4)-dafachronic acid (1a),(25R)-Delta(7)-dafachronic acid (2a), and (25R)-cholestenoic acid (3a), which represent potential ligands forthe hormonal receptor DAF-12 in Caenorhabditis elegans. Key-steps of our synthetic approach are amodified Clemmensen reduction of diosgenin (4a) and a double bond shift from the 5,6- to the 7,8-position. In the 25R-series, the Delta(7)-dafachronic acid 2a exhibits the highest hormonal activity.

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Year:  2009        PMID： 19225674     DOI： 10.1039/b817358c

Source DB:  PubMed          Journal:  Org Biomol Chem        ISSN： 1477-0520            Impact factor:   3.876


  5 in total

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Journal:  J Virol       Date:  2019-07-17       Impact factor: 5.103

2.  Synthesis of side-chain oxysterols and their enantiomers through cross-metathesis reactions of Δ22 steroids.

Authors:  David P Brownholland; Douglas F Covey
Journal:  Steroids       Date:  2017-03-12       Impact factor: 2.668

3.  DAF-12 regulates a connected network of genes to ensure robust developmental decisions.

Authors:  Daniel Hochbaum; Yue Zhang; Carsten Stuckenholz; Paul Labhart; Vassili Alexiadis; René Martin; Hans-Joachim Knölker; Alfred L Fisher
Journal:  PLoS Genet       Date:  2011-07-21       Impact factor: 5.917

4.  Heterologous expression and characterization of a 3-ketosteroid-∆1-dehydrogenase from Gordonia neofelifaecis and its utilization in the bioconversion of androst-4,9(11)-dien-3,17-dione.

Authors:  Weiyi Wang; Fanglan Ge; Caihong Ma; Jiang Li; Yao Ren; Wei Li; Jinsong Fu
Journal:  3 Biotech       Date:  2017-04-08       Impact factor: 2.406

5.  Endocannabinoids in Caenorhabditis elegans are essential for the mobilization of cholesterol from internal reserves.

Authors:  Celina Galles; Gastón M Prez; Sider Penkov; Sebastian Boland; Exequiel O J Porta; Silvia G Altabe; Guillermo R Labadie; Ulrike Schmidt; Hans-Joachim Knölker; Teymuras V Kurzchalia; Diego de Mendoza
Journal:  Sci Rep       Date:  2018-04-23       Impact factor: 4.379
  5 in total

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