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A Pyrene-Linked Cavity within a β-Barrel Protein Promotes an Asymmetric Diels-Alder Reaction
- Source :
- Angewandte Chemie International Edition. 56:13618-13622
- Publication Year :
- 2017
- Publisher :
- Wiley, 2017.
-
Abstract
- A unique π-expanded reaction cavity tethering a polycyclic moiety which provides a platform for substrate binding was constructed within the robust β-barrel structure of nitrobindin (NB). NB variants with cavities of different sizes and shapes are coupled with N-(1-pyrenyl)maleimide (Pyr) to prepare a series of NB-Pyr conjugates. The orientation of the pyrene moiety is fixed within the cavity by the coupling reaction. The fluorescent quenching analysis of NB-Pyr indicates that azachalcone (aza), which is a dienophile for a Diels-Alder (DA) reaction, is efficiently incorporated within the pyrene-linked reaction cavity by the aromatic interaction. The DA reaction between aza and cyclopentadiene proceeds within the reaction cavity of NB-Pyr in the presence of CuII ion in high yield and high enantio- and regioselectivity.
- Subjects :
- Hemeproteins
Models, Molecular
Cyclopentadiene
Stereochemistry
Arabidopsis
Cyclopentanes
010402 general chemistry
01 natural sciences
Catalysis
Coupling reaction
Maleimides
Heme-Binding Proteins
chemistry.chemical_compound
Moiety
Maleimide
Diels–Alder reaction
Aza Compounds
Pyrenes
Cycloaddition Reaction
Arabidopsis Proteins
010405 organic chemistry
Regioselectivity
General Medicine
General Chemistry
0104 chemical sciences
chemistry
Yield (chemistry)
Pyrene
Protein Conformation, beta-Strand
Copper
Subjects
Details
- ISSN :
- 14337851
- Volume :
- 56
- Database :
- OpenAIRE
- Journal :
- Angewandte Chemie International Edition
- Accession number :
- edsair.doi.dedup.....60ccc38fd01880576ccc2d12946bee67