Bioinspired Brønsted Acid-Promoted Regioselective Tryptophan Isoprenylations.


Journal

ACS omega
ISSN: 2470-1343
Titre abrégé: ACS Omega
Pays: United States
ID NLM: 101691658

Informations de publication

Date de publication:
27 Apr 2021
Historique:
received: 28 01 2021
accepted: 16 03 2021
entrez: 31 5 2021
pubmed: 1 6 2021
medline: 1 6 2021
Statut: epublish

Résumé

Tryptophan-containing isoprenoid indole alkaloid natural products are well known for their intricate structural architectures and significant biological activities. Nature employs dimethylallyl tryptophan synthases (DMATSs) or aromatic indole prenyltransferases (iPTs) to catalyze regio- and stereoselective prenylation of l-Trp. Regioselective synthetic routes that isoprenylate

Identifiants

pubmed: 34056238
doi: 10.1021/acsomega.1c00515
pmc: PMC8153798
doi:

Types de publication

Journal Article

Langues

eng

Pagination

10840-10858

Informations de copyright

© 2021 The Authors. Published byAmerican Chemical Society.

Déclaration de conflit d'intérêts

The authors declare no competing financial interest.

Références

Org Lett. 2016 Jan 4;18(1):28-31
pubmed: 26673685
J Org Chem. 2003 Sep 5;68(18):6944-51
pubmed: 12946134
Chem Rev. 2012 Jul 11;112(7):3641-716
pubmed: 22575049
Nat Prod Rep. 2011 Mar;28(3):496-510
pubmed: 21186384
J Org Chem. 2017 Aug 18;82(16):8769-8775
pubmed: 28745505
Appl Environ Microbiol. 2010 Jun;76(12):3898-903
pubmed: 20435769
Angew Chem Int Ed Engl. 2019 Dec 9;58(50):18069-18074
pubmed: 31587423
J Nat Prod. 2013 Apr 26;76(4):759-63
pubmed: 23547884
Biochem Biophys Res Commun. 1995 Nov 2;216(1):119-25
pubmed: 7488077
Chem Commun (Camb). 2019 Jul 25;55(58):8390-8393
pubmed: 31257394
J Am Chem Soc. 2004 Sep 22;126(37):11432-3
pubmed: 15366877
Nat Prod Rep. 2000 Aug;17(4):349-66
pubmed: 11014337
J Org Chem. 2014 Nov 7;79(21):10049-67
pubmed: 25244629
ACS Synth Biol. 2016 Jul 15;5(7):547-53
pubmed: 26641496
Biochemistry. 2013 Jun 18;52(24):4274-83
pubmed: 23705796
Nat Prod Rep. 2014 Oct;31(10):1328-38
pubmed: 25164781
Nat Prod Rep. 2019 Nov 13;36(11):1589-1605
pubmed: 30839047
Proc Natl Acad Sci U S A. 2004 Apr 13;101(15):5482-7
pubmed: 15067109
Angew Chem Int Ed Engl. 2014 Jun 10;53(24):6206-10
pubmed: 24777757
Arch Biochem Biophys. 1992 Jul;296(1):308-13
pubmed: 1605639
J Nat Prod. 2017 Aug 25;80(8):2371-2378
pubmed: 28803474
J Am Chem Soc. 2013 Feb 6;135(5):1895-902
pubmed: 23301871
Nat Prod Rep. 2015 Jan;32(1):88-101
pubmed: 25270661
Org Lett. 2011 May 20;13(10):2770-3
pubmed: 21513295
Acc Chem Res. 2020 Feb 18;53(2):425-446
pubmed: 31820922
J Am Chem Soc. 2020 Jun 10;142(23):10550-10556
pubmed: 32408745
Appl Microbiol Biotechnol. 2016 Dec;100(23):9943-9953
pubmed: 27311563
J Am Chem Soc. 2018 May 30;140(21):6710-6717
pubmed: 29750514
J Biol Chem. 2008 Jun 6;283(23):16068-76
pubmed: 18390548
Angew Chem Int Ed Engl. 2019 Aug 12;58(33):11534-11540
pubmed: 31206992
J Am Chem Soc. 2014 Dec 3;136(48):16756-9
pubmed: 25365411
Alkaloids Chem Biol. 2006;63:45-86
pubmed: 17133714
Nat Prod Rep. 2010 Jan;27(1):57-78
pubmed: 20024094
J Org Chem. 2018 Dec 7;83(23):14507-14517
pubmed: 30387357
ACS Chem Biol. 2014 Dec 19;9(12):2718-28
pubmed: 25303280
Phytochemistry. 2009 Oct-Nov;70(15-16):1746-57
pubmed: 19398116
Org Biomol Chem. 2015 Jul 14;13(26):7177-92
pubmed: 26022437
Chem Commun (Camb). 2012 May 7;48(36):4344-6
pubmed: 22447070
Beilstein J Org Chem. 2014 Aug 26;10:1991-8
pubmed: 25246958
Nat Rev Cancer. 2018 Jul;18(7):452-464
pubmed: 29643473
Nat Commun. 2019 Jun 27;10(1):2820
pubmed: 31249297

Auteurs

Tushar M Khopade (TM)

Departments of Chemistry & Biology, Indian Institute of Science Education and Research, Tirupati 517507, Andhra Pradesh India.

Kalyani Ajayan (K)

Departments of Chemistry & Biology, Indian Institute of Science Education and Research, Tirupati 517507, Andhra Pradesh India.

Swapnil S Joshi (SS)

Departments of Chemistry & Biology, Indian Institute of Science Education and Research, Tirupati 517507, Andhra Pradesh India.

Amy L Lane (AL)

Department of Chemistry, University of North Florida, Jacksonville 32224, Florida, United States.

Rajesh Viswanathan (R)

Departments of Chemistry & Biology, Indian Institute of Science Education and Research, Tirupati 517507, Andhra Pradesh India.
Department of Chemistry, University of North Florida, Jacksonville 32224, Florida, United States.

Classifications MeSH