NDLI: Palette of lipophilic bioconjugatable bacteriochlorins for construction of biohybrid light-harvesting architectures

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Engineering and applications of DNA-grafted polymer materials

Intriguing aspects of lanthanide luminescence

Revisiting the optical signatures of BODIPY with ab initio tools

Chelation-assisted Rh(iii)-catalyzed C2-selective oxidative C–H/C–H cross-coupling of indoles/pyrroles with heteroarenes

Ultra-sensitive chemosensors for Fe(iii) and explosives based on highly fluorescent oligofluoranthene

A dinuclear cyclometalated gold(iii)–phosphine complex targeting thioredoxin reductase inhibits hepatocellular carcinoma in vivo

Synthesis of spongistatin 2 employing a new route to the EF fragment

Scope and mechanism of asymmetric C(sp³)–H/C(Ar)–X coupling reactions: computational and experimental study

In situ preparation of a multifunctional chiral hybrid organic–inorganic catalyst for asymmetric multicomponent reactions

DNA-based asymmetric organometallic catalysis in water

Supersized contorted aromatics

“Push-no-pull” porphyrins for second harmonic generation imaging

Rapid and selective spiro-cyclisations of O-centred radicals onto aromatic acceptors

Palette of lipophilic bioconjugatable bacteriochlorins for construction of biohybrid light-harvesting architectures

Selective adsorption of ethylene over ethane and propylene over propane in the metal–organic frameworks M₂(dobdc) (M = Mg, Mn, Fe, Co, Ni, Zn)

Perfluorinated Taddol phosphoramidite as an L,Z-ligand on Rh(i) and Co(−i): evidence for bidentate coordination via metal–C₆F₅ interaction

Enhanced photocurrent generation by folding-driven H-aggregate formation

Recognition of glycosaminoglycan chemical patterns using an unbiased sensor array

RAFT dispersion polymerization in non-polar solvents: facile production of block copolymer spheres, worms and vesicles in n-alkanes

Selective affinity-based probe for oncogenic kinases suitable for live cell imaging

The role of viscosity on polymer ink transport in dip-pen nanolithography

Chiral β-iodoamines by urea-catalysed iodocyclization of trichloroacetimidates

MM quadruple bonds supported by cyanoacrylate ligands. Extending photon harvesting into the near infrared and studies of the MLCT states

Unexpected rearrangements in the synthesis of an unsymmetrical tridentate dianionic N-heterocyclic carbene

Poly(ethylene oxide)-block-polyphosphester-based paclitaxel conjugates as a platform for ultra-high paclitaxel-loaded multifunctional nanoparticles

CO₂ as a C₁-building block for the catalytic methylation of amines

¹⁹F-MRS/¹H-MRI dual-function probe for detection of β-galactosidase activity

High-intensity near-IR fluorescence in semiconducting polymer dots achieved by cascade FRET strategy

Decamethylscandocinium-hydrido-(perfluorophenyl)borate: fixation and tandem tris(perfluorophenyl)borane catalysed deoxygenative hydrosilation of carbon dioxide

Pd-catalyzed oxidative C–H/C–H cross-coupling of pyridines with heteroarenes

MegaStokes BODIPY-triazoles as environmentally sensitive turn-on fluorescent dyes

N-Heterocyclic carbene (NHC) catalyzed chemoselective acylation of alcohols in the presence of amines with various acylating reagents

Kinetics and thermodynamics of nitric oxide binding to transition metal complexes. Relationship to dioxygen binding

Anhydrides as α,β-unsaturated acyl ammonium precursors: isothiourea-promoted catalytic asymmetric annulation processes

Ruthenium-catalyzed ortho-C–H bond alkylation of aromatic amides with α,β-unsaturated ketones via bidentate-chelation assistance

Depleted uranium catalysts for chlorine production

Asymmetric Michael additions of α-cyanoacetates by soft Lewis acid/hard Brønsted acid catalysis: stereodivergency with bi- vs. monometallic catalysts

DNA functionalization of colloidal II–VI semiconductor nanowires for multiplex nanoheterostructures

Ligand-controlled β-selective C(sp³)–H arylation of N-Boc-piperidines

Efficient approach for the design of effective chiral quaternary phosphonium salts in asymmetric conjugate additions

Fast transimination in organic solvents in the absence of proton and metal catalysts. A key to imine metathesis catalyzed by primary amines under mild conditions

Total synthesis of (±)-leuconolam: intramolecular allylic silane addition to a maleimide carbonyl group

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Palette of lipophilic bioconjugatable bacteriochlorins for construction of biohybrid light-harvesting architectures

Content Provider	Royal Society of Chemistry (RSC)
Author	Niedzwiedzki, Dariusz M. Holten, Dewey Lindsey, Jonathan S. Kirmaier, Christine Bocian, David F. Jiao, Jieying Jiang, Jianbing Loach, Paul A. Reddy, Kanumuri Ramesh Harris, Michelle A. Yang, Eunkyung Krayer, Michael Parkes-Loach, Pamela S. Springer, Joseph W. Pandithavidana, Dinesh
Copyright Year	2013
Abstract	The challenge of creating both pigment building blocks and scaffolding to organize a large number of such pigments has long constituted a central impediment to the construction of artificial light-harvesting architectures. Light-harvesting (LH) antennas in photosynthetic bacteria are formed in a two-tiered self-assembly process wherein (1) a peptide dyad containing two bacteriochlorophyll a molecules forms, and (2) the dyads associate to form cyclic oligomers composed of 8 or 9 dyads in LH2 and 15 or 16 in LH1 of purple photosynthetic bacteria. While such antenna systems generally have near-quantitative transfer of excitation energy among pigments, only a fraction of the solar spectrum is typically absorbed. A platform architecture for study of light-harvesting phenomena has been developed that employs native photosynthetic peptide analogs, native bacteriochlorophyll a, and synthetic near-infrared-absorbing bacteriochlorins. Herein, the syntheses of 10 lipophilic bacteriochlorins are reported, of which 7 contain bioconjugatable handles (maleimide, iodoacetamide, formyl, carboxylic acid) for attachment to the peptide chassis. The bioconjugatable bacteriochlorins typically exhibit a long-wavelength absorption band in the range 710 to 820 nm, fluorescence yield of 0.1–0.2, and lifetime of the lowest singlet excited state of 2–5 ns. The α-helical structure of the native-like peptide is retained upon conjugation with a synthetic bacteriochlorin, as judged by single-reflection infrared studies. Static and time-resolved optical studies of the oligomeric biohybrid architectures in aqueous detergent solution reveal efficient (∼90%) excitation energy transfer from the attached bacteriochlorin to the native-like bacteriochlorophyll a sites. The biohybrid light-harvesting architectures thus exploit the self-constituting features of the natural systems yet enable versatile incorporation of members from a palette of synthetic chromophores, thereby opening the door to a wide variety of studies in artificial photosynthesis.
Starting Page	2036
Ending Page	2053
Page Count	18
File Format	HTM / HTML PDF
ISSN	20416520
Volume Number	4
Issue Number	5
Journal	Chemical Science
DOI	10.1039/c3sc22317e
Language	English
Publisher	Royal Society of Chemistry
Access Restriction	Open
Subject Keyword	Detergent Infrared Maleimide Fluorescence Chlorin Pigment Self-assembly Bacteriochlorophyll Carboxylic acid Absorption band Artificial photosynthesis Bacteria Iodoacetamide Photosynthesis Liquid hydrogen Peptide Lipophilicity
Content Type	Text
Resource Type	Article
Subject	Chemistry

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Amphiphilic, hydrophilic, or hydrophobic synthetic bacteriochlorins in biohybrid light-harvesting architectures: consideration of molecular designs

Near-infrared tunable bacteriochlorins equipped for bioorthogonal labeling

Amphiphilic, hydrophilic, or hydrophobic synthetic bacteriochlorins in biohybrid light-harvesting architectures: consideration of molecular designs

Bioconjugatable, PEGylated hydroporphyrins for photochemistry and photomedicine. Narrow-band, near-infrared-emitting bacteriochlorins

The structure and assembly of reaction centre-light-harvesting 1 complexes in photosynthetic bacteria.

Photosynthesis, pigment-protein complexes and electronic energy transport: simple models for complicated processes.

Is there a triplet state in photosynthesis?.

De Novo Synthesis of Bacteriochlorins Bearing Four Trideuteriomethyl Groups

Light-harvesting zinc chlorin-poly(4-vinylpyridine) complexes

Palette of lipophilic bioconjugatable bacteriochlorins for construction of biohybrid light-harvesting architectures

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Palette of lipophilic bioconjugatable bacteriochlorins for construction of biohybrid light-harvesting architectures