在生物碱生物合成的早期步骤中规避立体选择性。
Bypassing stereoselectivity in the early steps of alkaloid biosynthesis.
机构信息
MIT Department of Chemistry, 77 Massachusetts Avenue, 18-592, Cambridge, MA 02139, USA.
出版信息
Org Biomol Chem. 2009 Oct 21;7(20):4166-8. doi: 10.1039/b916027m. Epub 2009 Aug 13.
Abstract
Total synthesis of glycosylated seco-iridoid stereoisomers allows the identification and bypassing of the stereoselectivity of early steps in monoterpene indole alkaloid biosynthesis.
摘要
糖基化裂环环烯醚萜立体异构体的全合成允许鉴定和绕过单萜吲哚生物碱生物合成早期步骤的立体选择性。
相似文献
1
Bypassing stereoselectivity in the early steps of alkaloid biosynthesis.在生物碱生物合成的早期步骤中规避立体选择性。
Org Biomol Chem. 2009 Oct 21;7(20):4166-8. doi: 10.1039/b916027m. Epub 2009 Aug 13.
2
Substrate specificity and diastereoselectivity of strictosidine glucosidase, a key enzyme in monoterpene indole alkaloid biosynthesis.裂环马钱子苷葡萄糖苷酶的底物特异性和非对映选择性，单萜吲哚生物碱生物合成中的关键酶。
Bioorg Med Chem Lett. 2008 May 15;18(10):3095-8. doi: 10.1016/j.bmcl.2007.11.063. Epub 2007 Nov 22.
3
Glucosidases involved in indole alkaloid biosynthesis of Catharanthus cell cultures.参与长春花细胞培养物中吲哚生物碱生物合成的葡萄糖苷酶。
FEBS Lett. 1980 Feb 11;110(2):187-91. doi: 10.1016/0014-5793(80)80069-x.
4
Aza-tryptamine substrates in monoterpene indole alkaloid biosynthesis.单萜吲哚生物碱生物合成中的氮杂色胺底物。
Chem Biol. 2009 Dec 24;16(12):1225-9. doi: 10.1016/j.chembiol.2009.11.016.
5
Virus-induced gene silencing identifies Catharanthus roseus 7-deoxyloganic acid-7-hydroxylase, a step in iridoid and monoterpene indole alkaloid biosynthesis.病毒诱导的基因沉默鉴定长春花 7-去氧马钱子酸-7-羟化酶，该酶是裂环马钱子苷酸和单萜吲哚生物碱生物合成中的一步。
Plant J. 2013 Dec;76(5):754-65. doi: 10.1111/tpj.12330. Epub 2013 Oct 23.
6
A stereoselective hydroxylation step of alkaloid biosynthesis by a unique cytochrome P450 in Catharanthus roseus.长春花中生物碱生物合成的一种独特细胞色素 P450 的立体选择性羟化步骤。
J Biol Chem. 2011 May 13;286(19):16751-7. doi: 10.1074/jbc.M111.225383. Epub 2011 Mar 24.
7
Sarpagan bridge enzyme has substrate-controlled cyclization and aromatization modes.沙帕坦桥酶具有底物控制的环化和芳构化模式。
Nat Chem Biol. 2018 Aug;14(8):760-763. doi: 10.1038/s41589-018-0078-4. Epub 2018 Jun 25.
8
Homolog of tocopherol C methyltransferases catalyzes N methylation in anticancer alkaloid biosynthesis.生育酚 C 甲基转移酶同源物催化抗癌生物碱生物合成中的 N 甲基化。
Proc Natl Acad Sci U S A. 2010 Nov 2;107(44):18793-8. doi: 10.1073/pnas.1009003107. Epub 2010 Oct 18.
9
Molecular cloning and functional bacterial expression of a plant glucosidase specifically involved in alkaloid biosynthesis.一种专门参与生物碱生物合成的植物葡糖苷酶的分子克隆及功能性细菌表达
Phytochemistry. 2000 Aug;54(7):657-66. doi: 10.1016/s0031-9422(00)00175-8.
10
Opium poppy and Madagascar periwinkle: model non-model systems to investigate alkaloid biosynthesis in plants.罂粟和长春花：用于研究植物生物碱生物合成的模式与非模式系统
Plant J. 2008 May;54(4):763-84. doi: 10.1111/j.1365-313X.2008.03438.x.
引用本文的文献
1
Total Synthesis of (-)-Strictosidine and Interception of Aryne Natural Product Derivatives "Strictosidyne" and "Strictosamidyne".(-)-苦柯碱的全合成及芳炔天然产物衍生物“苦柯啶”和“苦柯赛因”的截获。
J Am Chem Soc. 2021 May 19;143(19):7471-7479. doi: 10.1021/jacs.1c02004. Epub 2021 May 6.
2
Aza-tryptamine substrates in monoterpene indole alkaloid biosynthesis.单萜吲哚生物碱生物合成中的氮杂色胺底物。
Chem Biol. 2009 Dec 24;16(12):1225-9. doi: 10.1016/j.chembiol.2009.11.016.
本文引用的文献
1
Partial purification and characterization of a NADPH dependent tetrahydroalstonine synthase from Catharanthus roseus cell suspension cultures.从长春花悬浮细胞培养物中纯化和表征 NADPH 依赖的四氢哈尔托宁合酶。
Plant Cell Rep. 1985 Aug;4(4):216-9. doi: 10.1007/BF00269293.
2
Strictosidine synthase: mechanism of a Pictet-Spengler catalyzing enzyme.严格乌头碱合酶：一种催化Pictet-Spengler反应的酶的作用机制
J Am Chem Soc. 2008 Jan 16;130(2):710-23. doi: 10.1021/ja077190z.
3
Substrate specificity and diastereoselectivity of strictosidine glucosidase, a key enzyme in monoterpene indole alkaloid biosynthesis.裂环马钱子苷葡萄糖苷酶的底物特异性和非对映选择性，单萜吲哚生物碱生物合成中的关键酶。
Bioorg Med Chem Lett. 2008 May 15;18(10):3095-8. doi: 10.1016/j.bmcl.2007.11.063. Epub 2007 Nov 22.
4
Molecular architecture of strictosidine glucosidase: the gateway to the biosynthesis of the monoterpenoid indole alkaloid family.士的宁苷葡萄糖苷酶的分子结构：单萜吲哚生物碱家族生物合成的关键途径
Plant Cell. 2007 Sep;19(9):2886-97. doi: 10.1105/tpc.106.045682. Epub 2007 Sep 21.
5
Chemistry and biology of monoterpene indole alkaloid biosynthesis.单萜吲哚生物碱生物合成的化学与生物学
Nat Prod Rep. 2006 Aug;23(4):532-47. doi: 10.1039/b512615k. Epub 2006 May 26.
6
The structure of Rauvolfia serpentina strictosidine synthase is a novel six-bladed beta-propeller fold in plant proteins.萝芙木严格定碱合酶的结构是植物蛋白中一种新型的六叶β-螺旋桨折叠结构。
Plant Cell. 2006 Apr;18(4):907-20. doi: 10.1105/tpc.105.038018. Epub 2006 Mar 10.
7
The Catharanthus alkaloids: pharmacognosy and biotechnology.长春花生物碱：生药学与生物技术
Curr Med Chem. 2004 Mar;11(5):607-28. doi: 10.2174/0929867043455846.
8
Assessment of the therapeutic activity of a combination of almitrine and raubasine on functional rehabilitation following ischaemic stroke.
Curr Med Res Opin. 2004 Mar;20(3):409-15. doi: 10.1185/030079904125003080.
9
Heterologous expression of a Rauvolfia cDNA encoding strictosidine glucosidase, a biosynthetic key to over 2000 monoterpenoid indole alkaloids.萝芙木编码异胡豆苷葡萄糖苷酶的cDNA的异源表达，异胡豆苷葡萄糖苷酶是2000多种单萜吲哚生物碱生物合成的关键。
Eur J Biochem. 2002 Apr;269(8):2204-13. doi: 10.1046/j.1432-1033.2002.02878.x.
10
Development of a highly efficient catalytic method for synthesis of vinyl ethers.一种用于合成乙烯基醚的高效催化方法的开发。
J Am Chem Soc. 2002 Feb 27;124(8):1590-1. doi: 10.1021/ja0173932.
Zotero 插件