guest ::
| Home > Publications database > One-Pot, Two-Step Hydroxylation of the Macrocyclic Diterpenoid β-Cembrenediol Catalyzed by P450 BM3 Mutants > print |
| Home > Publications database > One-Pot, Two-Step Hydroxylation of the Macrocyclic Diterpenoid β-Cembrenediol Catalyzed by P450 BM3 Mutants > print |
| 001 | 823900 | ||
| 005 | 20210129224902.0 | ||
| 024 | 7 | _ | |a 10.1002/cctc.201600973 |2 doi |
| 024 | 7 | _ | |a 1867-3880 |2 ISSN |
| 024 | 7 | _ | |a 1867-3899 |2 ISSN |
| 024 | 7 | _ | |a WOS:000397015100011 |2 WOS |
| 024 | 7 | _ | |a altmetric:13687668 |2 altmetric |
| 037 | _ | _ | |a FZJ-2016-06532 |
| 082 | _ | _ | |a 540 |
| 100 | 1 | _ | |a Le-Huu, Priska |0 P:(DE-HGF)0 |b 0 |
| 245 | _ | _ | |a One-Pot, Two-Step Hydroxylation of the Macrocyclic Diterpenoid β-Cembrenediol Catalyzed by P450 BM3 Mutants |
| 260 | _ | _ | |a Weinheim |c 2016 |b WILEY-VCH Verlag |
| 336 | 7 | _ | |a article |2 DRIVER |
| 336 | 7 | _ | |a Output Types/Journal article |2 DataCite |
| 336 | 7 | _ | |a Journal Article |b journal |m journal |0 PUB:(DE-HGF)16 |s 1484489836_25319 |2 PUB:(DE-HGF) |
| 336 | 7 | _ | |a ARTICLE |2 BibTeX |
| 336 | 7 | _ | |a JOURNAL_ARTICLE |2 ORCID |
| 336 | 7 | _ | |a Journal Article |0 0 |2 EndNote |
| 520 | _ | _ | |a Cytochrome P450 monooxygenases (P450s) are involved in the biosynthesis of a wide range of bioactive secondary metabolites. They often introduce several oxy functionalities at different positions of a substrate through multiple steps and produce a range of oxidized derivatives. Herein, we describe a one-pot two-step hydroxylation of the diterpenoid b-cembrenediol isolated from the plant Nicotiana tabacum. This 14-membered macrocycle shows neuroprotective effects and is, along with its oxidized derivatives, of pharmaceutical interest. Sequential hydroxylations catalyzed by the regioselective P450 BM3 mutants F87A/I263L and V78A/F87G yielded the epimeric (9S,10R/S)-b-cembrenetetraols with a diastereomeric ratio of 48:52. The replacement of the mutant V78A/F87G with L75A/ V78A/F87G in the second step improves the diastereomeric ratio up to 10:90. Absolute configurations of the newly introduced hydroxy groups were determined by quantum-mechanical calculations of NMR spectra. |
| 536 | _ | _ | |a 553 - Physical Basis of Diseases (POF3-553) |0 G:(DE-HGF)POF3-553 |c POF3-553 |f POF III |x 0 |
| 588 | _ | _ | |a Dataset connected to CrossRef |
| 700 | 1 | _ | |a Petrović, Dušan |0 P:(DE-Juel1)165744 |b 1 |u fzj |
| 700 | 1 | _ | |a Strodel, Birgit |0 P:(DE-Juel1)132024 |b 2 |u fzj |
| 700 | 1 | _ | |a Urlacher, Vlada B. |0 P:(DE-HGF)0 |b 3 |e Corresponding author |
| 773 | _ | _ | |a 10.1002/cctc.201600973 |0 PERI:(DE-600)2501161-3 |n 24 |p 3755-3761 |t ChemCatChem |v 8 |y 2016 |x 1867-3880 |
| 856 | 4 | _ | |u https://juser.fz-juelich.de/record/823900/files/One-Pot%2C%20Two-Step%20Hydroxylation%20of%20the%20Macrocyclic%20Diterpenoid%20%CE%B2-Cembrenediol%20Catalyzed%20by%20P450%20BM3%20Mutants_2016.pdf |y Restricted |
| 856 | 4 | _ | |u https://juser.fz-juelich.de/record/823900/files/One-Pot%2C%20Two-Step%20Hydroxylation%20of%20the%20Macrocyclic%20Diterpenoid%20%CE%B2-Cembrenediol%20Catalyzed%20by%20P450%20BM3%20Mutants_2016.pdf?subformat=pdfa |x pdfa |y Restricted |
| 909 | C | O | |o oai:juser.fz-juelich.de:823900 |p VDB |
| 910 | 1 | _ | |a Forschungszentrum Jülich |0 I:(DE-588b)5008462-8 |k FZJ |b 1 |6 P:(DE-Juel1)165744 |
| 910 | 1 | _ | |a Forschungszentrum Jülich |0 I:(DE-588b)5008462-8 |k FZJ |b 2 |6 P:(DE-Juel1)132024 |
| 913 | 1 | _ | |a DE-HGF |b Key Technologies |l BioSoft – Fundamentals for future Technologies in the fields of Soft Matter and Life Sciences |1 G:(DE-HGF)POF3-550 |0 G:(DE-HGF)POF3-553 |2 G:(DE-HGF)POF3-500 |v Physical Basis of Diseases |x 0 |4 G:(DE-HGF)POF |3 G:(DE-HGF)POF3 |
| 914 | 1 | _ | |y 2016 |
| 915 | _ | _ | |a JCR |0 StatID:(DE-HGF)0100 |2 StatID |b CHEMCATCHEM : 2015 |
| 915 | _ | _ | |a DBCoverage |0 StatID:(DE-HGF)0200 |2 StatID |b SCOPUS |
| 915 | _ | _ | |a DBCoverage |0 StatID:(DE-HGF)0300 |2 StatID |b Medline |
| 915 | _ | _ | |a DBCoverage |0 StatID:(DE-HGF)0310 |2 StatID |b NCBI Molecular Biology Database |
| 915 | _ | _ | |a DBCoverage |0 StatID:(DE-HGF)0600 |2 StatID |b Ebsco Academic Search |
| 915 | _ | _ | |a Peer Review |0 StatID:(DE-HGF)0030 |2 StatID |b ASC |
| 915 | _ | _ | |a DBCoverage |0 StatID:(DE-HGF)0199 |2 StatID |b Thomson Reuters Master Journal List |
| 915 | _ | _ | |a WoS |0 StatID:(DE-HGF)0111 |2 StatID |b Science Citation Index Expanded |
| 915 | _ | _ | |a DBCoverage |0 StatID:(DE-HGF)0150 |2 StatID |b Web of Science Core Collection |
| 915 | _ | _ | |a DBCoverage |0 StatID:(DE-HGF)1150 |2 StatID |b Current Contents - Physical, Chemical and Earth Sciences |
| 915 | _ | _ | |a IF < 5 |0 StatID:(DE-HGF)9900 |2 StatID |
| 920 | _ | _ | |l yes |
| 920 | 1 | _ | |0 I:(DE-Juel1)ICS-6-20110106 |k ICS-6 |l Strukturbiochemie |x 0 |
| 980 | _ | _ | |a journal |
| 980 | _ | _ | |a VDB |
| 980 | _ | _ | |a I:(DE-Juel1)ICS-6-20110106 |
| 980 | _ | _ | |a UNRESTRICTED |
| 981 | _ | _ | |a I:(DE-Juel1)IBI-7-20200312 |
| Library | Collection | CLSMajor | CLSMinor | Language | Author |
|---|