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Asymmetric Synthesis of (R)-1-Alkyl-Substituted Tetrahydro-ß-carbolines Catalyzed by Strictosidine Synthases.

التفاصيل البيبلوغرافية
العنوان: Asymmetric Synthesis of (R)-1-Alkyl-Substituted Tetrahydro-ß-carbolines Catalyzed by Strictosidine Synthases.
المؤلفون: Pressnitz D; Department of Chemistry, Organic und Bioorganic Chemistry, University of Graz, NAWI Graz, BioTechMed Graz, Heinrichstrasse 28, 8010, Graz, Austria., Fischereder EM; Department of Chemistry, Organic und Bioorganic Chemistry, University of Graz, NAWI Graz, BioTechMed Graz, Heinrichstrasse 28, 8010, Graz, Austria., Pletz J; Department of Chemistry, Organic und Bioorganic Chemistry, University of Graz, NAWI Graz, BioTechMed Graz, Heinrichstrasse 28, 8010, Graz, Austria., Kofler C; Department of Chemistry, Organic und Bioorganic Chemistry, University of Graz, NAWI Graz, BioTechMed Graz, Heinrichstrasse 28, 8010, Graz, Austria., Hammerer L; Department of Chemistry, Organic und Bioorganic Chemistry, University of Graz, NAWI Graz, BioTechMed Graz, Heinrichstrasse 28, 8010, Graz, Austria.; ACIB GmbH-Austrian Center of Industrial Biotechnology, Petersgasse 14, 8010, Graz, Austria., Hiebler K; Department of Chemistry, Organic und Bioorganic Chemistry, University of Graz, NAWI Graz, BioTechMed Graz, Heinrichstrasse 28, 8010, Graz, Austria., Lechner H; Department of Chemistry, Organic und Bioorganic Chemistry, University of Graz, NAWI Graz, BioTechMed Graz, Heinrichstrasse 28, 8010, Graz, Austria., Richter N; ACIB GmbH-Austrian Center of Industrial Biotechnology, Petersgasse 14, 8010, Graz, Austria., Eger E; Department of Chemistry, Organic und Bioorganic Chemistry, University of Graz, NAWI Graz, BioTechMed Graz, Heinrichstrasse 28, 8010, Graz, Austria., Kroutil W; Department of Chemistry, Organic und Bioorganic Chemistry, University of Graz, NAWI Graz, BioTechMed Graz, Heinrichstrasse 28, 8010, Graz, Austria.
المصدر: Angewandte Chemie (International ed. in English) [Angew Chem Int Ed Engl] 2018 Aug 13; Vol. 57 (33), pp. 10683-10687. Date of Electronic Publication: 2018 Jun 21.
نوع المنشور: Journal Article; Research Support, Non-U.S. Gov't
اللغة: English
بيانات الدورية: Publisher: Wiley-VCH Country of Publication: Germany NLM ID: 0370543 Publication Model: Print-Electronic Cited Medium: Internet ISSN: 1521-3773 (Electronic) Linking ISSN: 14337851 NLM ISO Abbreviation: Angew Chem Int Ed Engl
أسماء مطبوعة: Publication: <2004-> : Weinheim : Wiley-VCH
Original Publication: Weinheim/Bergstr. : New York, : Verlag Chemie ; Academic Press, c1962-
مواضيع طبية MeSH: Carbolines/*metabolism , Carbon-Nitrogen Lyases/*metabolism , Plant Proteins/*metabolism, Biocatalysis ; Carbolines/chemistry ; Catharanthus/enzymology ; Indole Alkaloids/chemistry ; Indole Alkaloids/metabolism ; Stereoisomerism ; Tryptamines/chemistry ; Tryptamines/metabolism
مستخلص: Stereoselective methods for the synthesis of tetrahydro-ß-carbolines are of significant interest due to the broad spectrum of biological activity of the target molecules. In the plant kingdom, strictosidine synthases catalyze the C-C coupling through a Pictet-Spengler reaction of tryptamine and secologanin to exclusively form the (S)-configured tetrahydro-ß-carboline (S)-strictosidine. Investigating the biocatalytic Pictet-Spengler reaction of tryptamine with small-molecular-weight aliphatic aldehydes revealed that the strictosidine synthases give unexpectedly access to the (R)-configured product. Developing an efficient expression method for the enzyme allowed the preparative transformation of various aldehydes, giving the products with up to >98 % ee. With this tool in hand, a chemoenzymatic two-step synthesis of (R)-harmicine was achieved, giving (R)-harmicine in 67 % overall yield in optically pure form.
(© 2018 The Authors. Published by Wiley-VCH Verlag GmbH & Co. KGaA.)
References: J Nat Prod. 2017 Apr 28;80(4):864-871. (PMID: 28218521)
Plant Cell Physiol. 2003 Apr;44(4):395-403. (PMID: 12721380)
Bioorg Med Chem Lett. 2006 May 1;16(9):2475-8. (PMID: 16481164)
Bioorg Med Chem. 2014 Oct 15;22(20):5633-7. (PMID: 24996997)
Org Process Res Dev. 2013 May 17;17(5):751-759. (PMID: 23794796)
Nat Methods. 2011 Sep 29;8(10):785-6. (PMID: 21959131)
Alkaloids Chem Biol. 2016;76:1-61. (PMID: 26827882)
J Org Chem. 2014 Aug 15;79(16):7380-90. (PMID: 25046801)
Org Lett. 2000 Jun 29;2(13):1955-1958. (PMID: 10891200)
ACS Chem Biol. 2017 Dec 15;12(12):3086-3092. (PMID: 29140075)
Angew Chem Int Ed Engl. 2018 Aug 13;57(33):10683-10687. (PMID: 29852524)
Curr Opin Chem Biol. 2014 Apr;19:180-92. (PMID: 24721252)
Curr Opin Chem Biol. 2012 Apr;16(1-2):142-9. (PMID: 22409961)
Chem Asian J. 2010 Nov 2;5(11):2400-4. (PMID: 20872397)
J Am Chem Soc. 2008 Jan 16;130(2):710-23. (PMID: 18081287)
Trends Biochem Sci. 2006 Oct;31(10):563-71. (PMID: 16919958)
Chem Commun (Camb). 2018 Feb 1;54(11):1323-1326. (PMID: 29345260)
J Am Chem Soc. 2006 Feb 1;128(4):1086-7. (PMID: 16433519)
Arch Biochem Biophys. 1992 May 1;294(2):717-23. (PMID: 1567228)
Nat Commun. 2017 Apr 03;8:14883. (PMID: 28368003)
J Ethnopharmacol. 2008 Feb 12;115(3):449-54. (PMID: 18054186)
Curr Opin Chem Biol. 2018 Apr;43:15-22. (PMID: 29100099)
Chem Biodivers. 2010 Apr;7(4):860-70. (PMID: 20397221)
Pharmacol Biochem Behav. 2012 Jul;102(1):133-8. (PMID: 22507912)
ACS Catal. 2016 Jul 1;6(7):4286-4311. (PMID: 27398261)
Org Lett. 2009 Aug 6;11(15):3238-41. (PMID: 19572756)
J Org Chem. 2008 Aug 15;73(16):6405-8. (PMID: 18616320)
FEBS Lett. 1988 Sep 12;237(1-2):40-4. (PMID: 3049153)
Chem Biol. 2015 Jul 23;22(7):898-906. (PMID: 26120001)
Biochemistry. 2017 Oct 10;56(40):5274-5277. (PMID: 28915025)
Trends Cell Biol. 1998 Oct;8(10):410-5. (PMID: 9789330)
Nat Chem Biol. 2010 Jun;6(6):408-10. (PMID: 20453862)
Neurosci Lett. 1996 Jul 19;212(3):183-6. (PMID: 8843103)
Biochim Biophys Acta. 2004 Oct 1;1702(1):121-4. (PMID: 15450856)
J Org Chem. 1998 Sep 4;63(18):6348-6354. (PMID: 11672269)
Chem Biol. 2007 Sep;14(9):979-85. (PMID: 17884630)
Curr Opin Chem Biol. 2015 Apr;25:115-23. (PMID: 25598537)
Angew Chem Int Ed Engl. 2011 Sep 5;50(37):8538-64. (PMID: 21830283)
J Am Chem Soc. 2012 Jan 25;134(3):1498-500. (PMID: 22229634)
Biochemistry. 1979 Aug 21;18(17):3760-3. (PMID: 476085)
Biochem J. 1995 Mar 1;306 ( Pt 2):571-80. (PMID: 7887913)
Chemistry. 2012 Mar 12;18(11):3148-52. (PMID: 22354859)
PLoS One. 2013 May 07;8(5):e63442. (PMID: 23667620)
Bioorg Med Chem Lett. 2017 Feb 15;27(4):893-896. (PMID: 28119023)
J Am Chem Soc. 2007 Nov 7;129(44):13404-5. (PMID: 17941641)
J Org Chem. 2011 Nov 4;76(21):8907-12. (PMID: 21950549)
Org Lett. 2009 Feb 19;11(4):887-90. (PMID: 19178157)
Angew Chem Int Ed Engl. 2013 Sep 16;52(38):9980-4. (PMID: 23913777)
J Am Chem Soc. 2013 Jul 24;135(29):10863-9. (PMID: 23808566)
Nucleic Acids Res. 1990 Aug 25;18(16):4939. (PMID: 2395663)
Chem Rev. 2017 Apr 26;117(8):5226-5333. (PMID: 27936626)
Tetrahedron Lett. 2012 Feb 29;53(9):1071-1074. (PMID: 22966211)
Angew Chem Int Ed Engl. 2007;46(39):7485-7. (PMID: 17702087)
Plant Mol Biol. 1992 Apr;18(6):1121-31. (PMID: 1600148)
Chem Rev. 2016 Oct 12;116(19):12369-12465. (PMID: 27680197)
Angew Chem Int Ed Engl. 2017 Jun 19;56(26):7440-7443. (PMID: 28466512)
Tetrahedron Lett. 2010 Aug 18;51(33):4400-4402. (PMID: 20689670)
فهرسة مساهمة: Keywords: Pictet-Spengler reaction; asymmetric catalysis; biocatalysis; strictosidine Synthases; tetrahydro-β-carbolines
المشرفين على المادة: 0 (Carbolines)
0 (Indole Alkaloids)
0 (Plant Proteins)
0 (Tryptamines)
0 (harmicine)
422ZU9N5TV (tryptamine)
EC 4.3.- (Carbon-Nitrogen Lyases)
EC 4.3.3.2 (strictosidine synthetase)
تواريخ الأحداث: Date Created: 20180601 Date Completed: 20190808 Latest Revision: 20231103
رمز التحديث: 20231215
مُعرف محوري في PubMed: PMC6146909
DOI: 10.1002/anie.201803372
PMID: 29852524
قاعدة البيانات: MEDLINE
الوصف
تدمد:1521-3773
DOI:10.1002/anie.201803372