Chemoenzymatic Total Synthesis of Deoxy-, epi-, and Podophyllotoxin and a Biocatalytic Kinetic Resolution of Dibenzylbutyrolactones.
2-oxoglutarate-dependent dioxygenases
biocatalysis
lignans
podophyllotoxin
total synthesis
Journal
Angewandte Chemie (International ed. in English)
ISSN: 1521-3773
Titre abrégé: Angew Chem Int Ed Engl
Pays: Germany
ID NLM: 0370543
Informations de publication
Date de publication:
11 06 2019
11 06 2019
Historique:
received:
23
01
2019
pubmed:
29
3
2019
medline:
9
9
2020
entrez:
29
3
2019
Statut:
ppublish
Résumé
Podophyllotoxin is probably the most prominent representative of lignan natural products. Deoxy-, epi-, and podophyllotoxin, which are all precursors to frequently used chemotherapeutic agents, were prepared by a stereodivergent biotransformation and a biocatalytic kinetic resolution of the corresponding dibenzylbutyrolactones with the same 2-oxoglutarate-dependent dioxygenase. The reaction can be conducted on 2 g scale, and the enzyme allows tailoring of the initial, "natural" structure and thus transforms various non-natural derivatives. Depending on the substitution pattern, the enzyme performs an oxidative C-C bond formation by C-H activation or hydroxylation at the benzylic position prone to ring closure.
Identifiants
pubmed: 30920120
doi: 10.1002/anie.201900926
pmc: PMC6563474
doi:
Substances chimiques
Lactones
0
Podophyllotoxin
L36H50F353
Types de publication
Journal Article
Research Support, Non-U.S. Gov't
Langues
eng
Sous-ensembles de citation
IM
Pagination
8226-8230Subventions
Organisme : Austrian Science Fund
ID : P 31276-B21
Pays : International
Informations de copyright
© 2019 The Authors. Published by Wiley-VCH Verlag GmbH & Co. KGaA.
Références
Biochemistry. 2011 Mar 15;50(10):1739-54
pubmed: 21250661
Angew Chem Int Ed Engl. 2015 Apr 20;54(17):5117-21
pubmed: 25712404
J Org Chem. 2018 Jul 20;83(14):7407-7415
pubmed: 29771530
Chem Rev. 2010 Feb 10;110(2):932-48
pubmed: 19769330
Nat Chem Biol. 2013 May;9(5):285-8
pubmed: 23594772
Eur J Cancer. 1998 Sep;34(10):1514-21
pubmed: 9893622
Org Lett. 2011 May 20;13(10):2594-7
pubmed: 21488628
Nat Chem Biol. 2008 Mar;4(3):186-93
pubmed: 18277980
Biochemistry. 2011 Jul 12;50(27):6063-72
pubmed: 21648411
Angew Chem Weinheim Bergstr Ger. 2015 Apr 20;127(17):5206-5210
pubmed: 27546918
Chem Rev. 2004 Feb;104(2):939-86
pubmed: 14871146
Adv Synth Catal. 2013 Sep 16;355(13):2499-2505
pubmed: 24415960
J Bacteriol. 1997 Sep;179(18):5677-83
pubmed: 9294421
Angew Chem Int Ed Engl. 2017 Jul 24;56(31):8942-8973
pubmed: 28407390
Angew Chem Int Ed Engl. 2011 Apr 4;50(15):3362-74
pubmed: 21413105
Angew Chem Int Ed Engl. 2012 Apr 2;51(14):3428-31
pubmed: 22374809
Curr Opin Chem Biol. 2013 Aug;17(4):532-6
pubmed: 23870699
Biochem Biophys Res Commun. 2009 Dec 18;390(3):506-10
pubmed: 19850012
Chem Rev. 2014 Apr 9;114(7):3919-62
pubmed: 24400737
Acc Chem Res. 2012 Jun 19;45(6):826-39
pubmed: 22017496
Curr Opin Biotechnol. 2019 Dec;60:29-38
pubmed: 30583278
Appl Environ Microbiol. 2011 Oct;77(19):6926-30
pubmed: 21821743
Angew Chem Int Ed Engl. 2019 Jun 11;58(24):8226-8230
pubmed: 30920120
Appl Environ Microbiol. 1999 Sep;65(9):4028-31
pubmed: 10473412
Biosci Biotechnol Biochem. 2000 Apr;64(4):746-50
pubmed: 10830487
Angew Chem Int Ed Engl. 2018 Apr 23;57(18):5037-5041
pubmed: 29481729
Nature. 2019 Jan;565(7737):67-72
pubmed: 30568304
Biochem J. 1996 Jan 1;313 ( Pt 1):185-91
pubmed: 8546682
Org Lett. 2019 Jan 4;21(1):228-232
pubmed: 30550285
Org Lett. 2018 Mar 16;20(6):1651-1654
pubmed: 29508607
Chem Soc Rev. 2011 Sep;40(9):4740-61
pubmed: 21666903
Science. 2015 Sep 11;349(6253):1224-8
pubmed: 26359402
Enzyme Microb Technol. 1993 Dec;15(12):1051-6
pubmed: 7505594
Appl Microbiol Biotechnol. 2010 Oct;88(3):719-26
pubmed: 20665018
Chem Pharm Bull (Tokyo). 2003 Jul;51(7):848-50
pubmed: 12843593
Chemistry. 2017 Sep 7;23(50):12040-12063
pubmed: 28514518
Appl Microbiol Biotechnol. 2011 Mar;89(6):1929-38
pubmed: 21069315
J Inorg Biochem. 2006 Apr;100(4):644-69
pubmed: 16513174
Appl Environ Microbiol. 1996 Jun;62(6):1903-7
pubmed: 16535329
Appl Microbiol Biotechnol. 2014 May;98(9):3869-76
pubmed: 24682483
Angew Chem Int Ed Engl. 2014 May 5;53(19):4750-2
pubmed: 24711286
J Biol Chem. 2013 Jun 14;288(24):17065-73
pubmed: 23632016
Org Biomol Chem. 2009 Oct 7;7(19):4082-7
pubmed: 19763315
J Am Chem Soc. 2008 Oct 29;130(43):14022-3
pubmed: 18828590
Proc Natl Acad Sci U S A. 2005 Jul 19;102(29):10111-6
pubmed: 16002467
Chemistry. 2017 Apr 3;23(19):4467-4526
pubmed: 27726183
J Org Chem. 2019 May 3;84(9):5831-5837
pubmed: 30920215
Biochim Biophys Acta. 2016 May;1864(5):453-70
pubmed: 26845569
J Am Chem Soc. 2018 Jan 24;140(3):1165-1169
pubmed: 29283572