高效的化学酶法合成 Rugulactone 的方法。
An Efficient Chemoenzymatic Approach towards the Synthesis of Rugulactone.
机构信息
Department of Chemistry, University of Crete, Vasilika Vouton, 71003 Heraklion, Crete, Greece.
出版信息
Molecules. 2018 Mar 12;23(3):640. doi: 10.3390/molecules23030640.
Abstract
Rugulactone is a natural product isolated from the plant . It has shown very important biological activity as an inhibitor of the nuclear factor κB (NF-κB) activation pathway. A new chemoenzymatic approach towards the synthesis of rugulactone is presented here. The chirality, induced to the key intermediate by a stereoselective enzymatic reduction utilizing NADPH-dependent ketoreductase, is described in detail.
摘要
瑞格芦亭是一种从植物中分离得到的天然产物。它作为核因子-κB（NF-κB）激活途径抑制剂显示出非常重要的生物学活性。本文介绍了一种新的化学酶法合成瑞格芦亭的方法。详细描述了利用 NADPH 依赖的酮还原酶进行立体选择性酶促还原，在关键中间体中诱导的手性。
相似文献
1
An Efficient Chemoenzymatic Approach towards the Synthesis of Rugulactone.
Molecules. 2018 Mar 12;23(3):640. doi: 10.3390/molecules23030640.
2
Inhibitors of the NF-kappaB activation pathway from Cryptocarya rugulosa.
J Nat Prod. 2009 Mar 27;72(3):336-9. doi: 10.1021/np800350x.
3
Rugulactone and its analogues exert antibacterial effects through multiple mechanisms including inhibition of thiamine biosynthesis.
Chembiochem. 2012 Jul 9;13(10):1439-46. doi: 10.1002/cbic.201200265. Epub 2012 May 31.
4
Stereoselective synthesis of both enantiomers of rugulactone.
J Org Chem. 2011 May 6;76(9):3463-9. doi: 10.1021/jo2004583. Epub 2011 Apr 5.
5
Stereoselective synthesis and biological evaluation of (R)-rugulactone, (6R)-((4R)-hydroxy-6-phenyl-hex-2-enyl)-5,6-dihydro-pyran-2-one and its 4S epimer.
Eur J Med Chem. 2010 Oct;45(10):4657-63. doi: 10.1016/j.ejmech.2010.07.036. Epub 2010 Jul 24.
6
Rugulactone derivatives act as inhibitors of NF-κB activation and modulates the transcription of NF-κB dependent genes in MDA-MB-231cells.
Bioorg Med Chem Lett. 2014 Mar 1;24(5):1389-96. doi: 10.1016/j.bmcl.2014.01.030. Epub 2014 Jan 20.
7
5,6-Dihydro-α-pyrones from the leaves of Cryptocarya pulchinervia (Lauraceae).
J Nat Med. 2020 Jun;74(3):584-590. doi: 10.1007/s11418-020-01397-7. Epub 2020 Mar 23.
8
A Sequential Umpolung/Enzymatic Dynamic Kinetic Resolution Strategy for the Synthesis of γ-Lactones.
Chemistry. 2020 May 7;26(26):5794-5798. doi: 10.1002/chem.202000747. Epub 2020 Apr 24.
9
Enantioselective Reduction of α,β-Unsaturated Ketones and Aryl Ketones by Perakine Reductase.
Org Lett. 2019 Jun 21;21(12):4411-4414. doi: 10.1021/acs.orglett.9b00950. Epub 2019 May 2.
10
A concise and straightforward total synthesis of (+/-)-salinosporamide A, based on a biosynthesis model.
Org Biomol Chem. 2008 Aug 7;6(15):2782-9. doi: 10.1039/b803818j. Epub 2008 May 29.
引用本文的文献
1
Recent Advances in the Stereoselective Total Synthesis of Natural Pyranones Having Long Side Chains.
Molecules. 2020 Apr 20;25(8):1905. doi: 10.3390/molecules25081905.
本文引用的文献
1
A facile stereoselective total synthesis of (R)-rugulactone.
ISRN Org Chem. 2014 Mar 30;2014:767954. doi: 10.1155/2014/767954. eCollection 2014.
2
Rugulactone derivatives act as inhibitors of NF-κB activation and modulates the transcription of NF-κB dependent genes in MDA-MB-231cells.
Bioorg Med Chem Lett. 2014 Mar 1;24(5):1389-96. doi: 10.1016/j.bmcl.2014.01.030. Epub 2014 Jan 20.
3
Assignment of the absolute configuration of polyfunctional compounds by NMR using chiral derivatizing agents.
Chem Rev. 2012 Aug 8;112(8):4603-41. doi: 10.1021/cr2003344. Epub 2012 Jun 1.
4
Rugulactone and its analogues exert antibacterial effects through multiple mechanisms including inhibition of thiamine biosynthesis.
Chembiochem. 2012 Jul 9;13(10):1439-46. doi: 10.1002/cbic.201200265. Epub 2012 May 31.
5
Enzymatic reductions for the regio- and stereoselective synthesis of hydroxy-keto esters and dihydroxy esters.
Org Lett. 2012 Apr 6;14(7):1792-5. doi: 10.1021/ol3003833. Epub 2012 Mar 12.
6
Stereoselective synthesis of both enantiomers of rugulactone.
J Org Chem. 2011 May 6;76(9):3463-9. doi: 10.1021/jo2004583. Epub 2011 Apr 5.
7
A two-step, one-pot enzymatic synthesis of 2-substituted 1,3-diols.
J Org Chem. 2010 Dec 17;75(24):8658-61. doi: 10.1021/jo101519t. Epub 2010 Nov 18.
8
Studies in chemotherapy; antithyroid compounds; synthesis of 5- and 6-substituted 2-thiouracils from beta-oxoesters and thiourea.
J Am Chem Soc. 1945 Dec;67:2197-2200. doi: 10.1021/ja01228a042.
9
Stereoselective synthesis and biological evaluation of (R)-rugulactone, (6R)-((4R)-hydroxy-6-phenyl-hex-2-enyl)-5,6-dihydro-pyran-2-one and its 4S epimer.
Eur J Med Chem. 2010 Oct;45(10):4657-63. doi: 10.1016/j.ejmech.2010.07.036. Epub 2010 Jul 24.
10
Inhibitors of the NF-kappaB activation pathway from Cryptocarya rugulosa.
J Nat Prod. 2009 Mar 27;72(3):336-9. doi: 10.1021/np800350x.
Zotero 插件