Concave reagents

Lüning, Ulrich; Baumstark, Roland; Wangnick, C.; Muller, M.; Schyja, W.; Gerst, Matthias; Gelbert, Markus

doi:10.1351/pac199365030527

Cited by 13 publications

(4 citation statements)

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“…From the log K ass values obtained for each substrate, it is clear that ImH (log K ass = 6.1 ± 0.2) and 2-MeImH (log K ass = 7.3 ± 0.3) develop additional interactions with the host when compared to N -MeIm (log K ass = 4.7 ± 0.2) or Py (log K ass = 3.3 ± 0.2). Phen pocket type derivatives have been studied as concave bases and are considered H-bond acceptors, especially when hidden in a hydrophobic cavity …”

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confidence: 99%

Side Selection of the Fifth Coordinate with a Single Strapped Zinc(II) Porphyrin Host: Full Characterization of Two Imidazole Complexes

et al. 1997

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confidence: 99%

Side Selection of the Fifth Coordinate with a Single Strapped Zinc(II) Porphyrin Host: Full Characterization of Two Imidazole Complexes

et al. 1997

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“…Based on the above, the distal site selectivity of 3Zn-(TMe-b-CD) 2 and the enhanced binding of ImH vs. N-Im can be attributed to the formation of a hydrogen bond between the ImH and the phenanthroline, in addition to metal-ligand binding. The TMe-b-CDs provide a microscopically apolar environment [18] that protects the hydrogen bonding site from the aqueous media, similar to the concept of concave phenanthroline bases established by Lüning et al [19].…”

Section: Resultsmentioning

confidence: 99%

Hydrogen bond directed molecular recognition in water in a strapped-porphyrin-cyclodextrin assembly

Kitagishi

Ohara

Shimoji

et al. 2021

Porphyrin Science by Women

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A water soluble, phenanthroline-strapped zinc porphyrin bearing four arylsulfonate groups formed a stable host-guest complex with two per-O-methylated b-cyclodextrin cavities. In the host-guest assembly, the zinc porphyrin was capable of binding imidazole within the cavity between the zinc(II) ion and the phenanthroline strap in an aqueous medium. The formation of a hydrogen bond between the imidazole NH and the nitrogen atoms of the phenanthroline was an essential element of the binding event, as shown by comparative binding studies with a non-strapped tetrasulfonated zinc porphyrin and with N-methylimidazole. This hydrogen bonding in an aqueous medium was possible due to the protected hydrophobic environment created by the cyclodextrins around the phenanthroline strap. This type of binding event may provide a biomimetic approach to study water soluble hemeprotein models.

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Section: Resultsmentioning

confidence: 99%

Hydrogen bond directed molecular recognition in water in a strapped-porphyrin-cyclodextrin assembly

Kitagishi

Ohara

Shimoji

et al. 2019

J. Porphyrins Phthalocyanines

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A water soluble, phenanthroline-strapped zinc porphyrin bearing four arylsulfonate groups formed a stable host–guest complex with two per-[Formula: see text]-methylated [Formula: see text]-cyclodextrin cavities. In the host–guest assembly, the zinc porphyrin was capable of binding imidazole within the cavity between the zinc(II) ion and the phenanthroline strap in an aqueous medium. The formation of a hydrogen bond between the imidazole NH and the nitrogen atoms of the phenanthroline was an essential element of the binding event, as shown by comparative binding studies with a non-strapped tetrasulfonated zinc porphyrin and with [Formula: see text]-methylimidazole. This hydrogen bonding in an aqueous medium was possible due to the protected hydrophobic environment created by the cyclodextrins around the phenanthroline strap. This type of binding event may provide a biomimetic approach to study water soluble heme protein models.

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Concave reagents

Abstract: Abstract

Cited by 13 publications

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Side Selection of the Fifth Coordinate with a Single Strapped Zinc(II) Porphyrin Host: Full Characterization of Two Imidazole Complexes

Side Selection of the Fifth Coordinate with a Single Strapped Zinc(II) Porphyrin Host: Full Characterization of Two Imidazole Complexes

Hydrogen bond directed molecular recognition in water in a strapped-porphyrin-cyclodextrin assembly

Hydrogen bond directed molecular recognition in water in a strapped-porphyrin-cyclodextrin assembly

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