David O’Hagan
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View article: On the Nature of Improper Hydrogen Bonding in RCH <sub>2</sub> F and RCHF <sub>2</sub> Motifs
On the Nature of Improper Hydrogen Bonding in RCH <sub>2</sub> F and RCHF <sub>2</sub> Motifs Open
The RCH 2 F and RCHF 2 groups are substituents of interest in medicinal and agrochemicals products. They have a polar aspect relative to the methyl (RCH 3 ) or trifluoromethyl (RCF 3 ) groups which results in a lowering of Log P's (water a…
View article: Bioactivity Profiles of Progressively Ring‐Fluorinated Cyclohexyl Motifs in the WKYMVm Peptide as Formylpeptide FPR2 Agonists and in Keto‐Piperazines as Antitrypanosome Agents
Bioactivity Profiles of Progressively Ring‐Fluorinated Cyclohexyl Motifs in the WKYMVm Peptide as Formylpeptide FPR2 Agonists and in Keto‐Piperazines as Antitrypanosome Agents Open
A series of all‐ cis ‐ring‐fluorinated cyclohexylalanines with progressively increasing levels of vicinal fluorines, as well as 4‐fluorophenylalanine and pentafluoroarylphenylalanine is introduced into the WKYMVm peptide in place of its ty…
View article: Performance of semiempirical DFT methods for the supramolecular assembly of Janus-face cyclohexanes
Performance of semiempirical DFT methods for the supramolecular assembly of Janus-face cyclohexanes Open
Compound protocols of DFT and GFN-xTB methods provide cost-efficient and accurate tools for computational modelling of Janus-face cyclohexane systems.
View article: Synthesis of Janus All-<i>Cis</i> Tetrafluorocyclohexanes Carrying 1,4-Diether Motifs
Synthesis of Janus All-<i>Cis</i> Tetrafluorocyclohexanes Carrying 1,4-Diether Motifs Open
Nucleophilic aromatic substitutions (SNAr) of alkoxides on pentafluoroaryl ethers are explored as a first step in a synthesis sequence to generate all-cis 2,3,5,6-tetrafluorocyclohexyl-1,4-dialkyl ethers 1. The SNAr reaction was explored b…
View article: Exploring Fluorinase Substrate Tolerance at C‐2 of SAM
Exploring Fluorinase Substrate Tolerance at C‐2 of SAM Open
The fluorinase enzyme (EC 2.5.1.63) utilises fluoride ion and S‐adenosyl‐L‐methionine (SAM) as substrates for conversion to 5′‐fluoro‐5′‐deoxy‐adenosine (5′‐FDA) and L‐methionine (L‐Met). The enzyme has a very strict substrate specificity,…
View article: Halogenated Adenine and Adenosine Natural Products in <i>Streptomyces</i> sp. JCM9888
Halogenated Adenine and Adenosine Natural Products in <i>Streptomyces</i> sp. JCM9888 Open
Ascamycin 1 and dealanylascamycin 2 are adenosine containing nucleoside antibiotics carrying the rare 5’‐ O ‐sulfamoyl ribose motif and a chlorine atom attached to C2 of the adenine ring. Gene knockouts (Δ acmK and Δ acmJ ) in the producin…
View article: Synthesis and Analysis of <i>(γ,γ’,γ’’</i>‐Trifluoro)neopentyl (TFNP) Aryl Ethers as a Polar Fluoroaliphatic Motif
Synthesis and Analysis of <i>(γ,γ’,γ’’</i>‐Trifluoro)neopentyl (TFNP) Aryl Ethers as a Polar Fluoroaliphatic Motif Open
A route is developed to (γ,γ’,γ’’’ ‐trifluoro)neopentyl (TFNP) aryl ethers to extend the methods for the introduction of the tert ‐butyl group, carrying a fluorine on each of the methyl substituents. The route combines neopentyltosylate 3 …
View article: Conformational Analysis Explores the Role of Electrostatic Nonclassical CF···HC Hydrogen Bonding Interactions in Selectively Halogenated Cyclohexanes
Conformational Analysis Explores the Role of Electrostatic Nonclassical CF···HC Hydrogen Bonding Interactions in Selectively Halogenated Cyclohexanes Open
The conformational equilibria of selectively halogenated cyclohexanes are explored both experimentally (VT-NMR) for 1,1,4,-trifluorocyclohexane 7 and by computational analysis (M06-2X/aug-cc-pVTZ level), with the latter approach extending …
View article: Efficient biotransformations in <i>Cunninghamella elegans</i> and <i>Streptomyces sp.</i> JCM9888 of selectively fluorinated benzoic acids to the corresponding benzamides and benzyl alcohols
Efficient biotransformations in <i>Cunninghamella elegans</i> and <i>Streptomyces sp.</i> JCM9888 of selectively fluorinated benzoic acids to the corresponding benzamides and benzyl alcohols Open
Support was received from the Commonwealth Scholarship Council for a Split Site Studentship (OO) and also from the Royal Society of Chemistry for a travel Grant (C.I).
View article: 3′-<i>O</i>-β-Glucosyl-4′,5′-didehydro-5′-deoxyadenosine Is a Natural Product of the Nucleocidin Producers <i>Streptomyces virens</i> and <i>Streptomyces calvus</i>
3′-<i>O</i>-β-Glucosyl-4′,5′-didehydro-5′-deoxyadenosine Is a Natural Product of the Nucleocidin Producers <i>Streptomyces virens</i> and <i>Streptomyces calvus</i> Open
3'-O-β-Glucosyl-4',5'-didehydro-5'-deoxyadenosine 13 is identified as a natural product of Streptomyces calvus and Streptomyces virens. It is also generated in vitro by direct β-glucosylation of 4',5'-didehydro-5'-deoxyadenosine 12 with th…
View article: CCDC 2259688: Experimental Crystal Structure Determination
CCDC 2259688: Experimental Crystal Structure Determination Open
An entry from the Cambridge Structural Database, the world’s repository for small molecule crystal structures. The entry contains experimental data from a crystal diffraction study. The deposited dataset for this entry is freely available …
View article: CCDC 2259690: Experimental Crystal Structure Determination
CCDC 2259690: Experimental Crystal Structure Determination Open
An entry from the Cambridge Structural Database, the world’s repository for small molecule crystal structures. The entry contains experimental data from a crystal diffraction study. The deposited dataset for this entry is freely available …
View article: CCDC 2270745: Experimental Crystal Structure Determination
CCDC 2270745: Experimental Crystal Structure Determination Open
An entry from the Cambridge Structural Database, the world’s repository for small molecule crystal structures. The entry contains experimental data from a crystal diffraction study. The deposited dataset for this entry is freely available …
View article: Aryl (β,β′,β″-Trifluoro)-<i>tert</i>-butyl: A Candidate Motif for the Discovery of Bioactives
Aryl (β,β′,β″-Trifluoro)-<i>tert</i>-butyl: A Candidate Motif for the Discovery of Bioactives Open
The (β,β',β″-trifluoro)-tert-butyl (TFTB) group has received very little attention in the literature. This work presents a direct synthesis of this group and explores its properties. The TFTB group arises when the methyl groups of a tert-b…
View article: Direct syntheses of stereoisomers of 3-fluoro GABA and β-fluoroamine analogues of the calcium receptor (CaR) agonists, cinacalcet, tecalcet, fendiline and NPS R-467
Direct syntheses of stereoisomers of 3-fluoro GABA and β-fluoroamine analogues of the calcium receptor (CaR) agonists, cinacalcet, tecalcet, fendiline and NPS R-467 Open
Synthetic routes following a sequential MacMillan organocatalytic asymmetric α-fluorination protocol for aldehydes and then reductive amination, have allowed ready access to bioactive β-fluoroamines. The approach is demonstrated with a sho…
View article: Lateral dipole moments induced by all-cis-pentafluorocyclohexyl groups cause unanticipated effects in self-assembled monolayers
Lateral dipole moments induced by all-cis-pentafluorocyclohexyl groups cause unanticipated effects in self-assembled monolayers Open
All- cis -hexafluoro- and all-cis-pentafluoro-cyclohexane (PFCH) derivatives are new kinds of materials, the structures and properties of which are dominated by the highly dipolar Janus-face motif. Here, we report on the effects of integra…
View article: Direct syntheses of stereoisomers of 3-fluoro GABA and β-fluoroamine analogues of the calcium receptor (CaR) agonists, cinacalcet, tecalcet, fendilines and NPS R-467
Direct syntheses of stereoisomers of 3-fluoro GABA and β-fluoroamine analogues of the calcium receptor (CaR) agonists, cinacalcet, tecalcet, fendilines and NPS R-467 Open
Synthetic routes following a sequential MacMillan organocatalytic asymmetric a-fluorination protocol for aldehydes and then reductive amination, has allowed ready access to bioactive b-fluoroamines. The approach is demonstrated with a shor…
View article: CCDC 2253285: Experimental Crystal Structure Determination
CCDC 2253285: Experimental Crystal Structure Determination Open
An entry from the Cambridge Structural Database, the world’s repository for small molecule crystal structures. The entry contains experimental data from a crystal diffraction study. The deposited dataset for this entry is freely available …
View article: [3-Methoxy-5-(methoxycarbonyl)isoxazol-4-yl](4-methoxyphenyl)iodonium 2,2,2-trifluoroacetate
[3-Methoxy-5-(methoxycarbonyl)isoxazol-4-yl](4-methoxyphenyl)iodonium 2,2,2-trifluoroacetate Open
A new isoxazole-based iodonoium salt, C 13 H 13 INO 5 + ·C 2 F 3 O 2 − , has been synthesized and structurally characterized. In the crystal, ions are linked by short I...O contacts to form a neutral tetra-ion aggregate. These combine with…
View article: The Emergence and Properties of Selectively Fluorinated ‘Janus’ Cyclohexanes
The Emergence and Properties of Selectively Fluorinated ‘Janus’ Cyclohexanes Open
This account describes the evolution of a research programme that started by linking fluoromethylene (−CHF−) groups along aliphatic chains and then progressing to alicyclic rings with contiguous fluorine atoms. Different stereoisomers of a…
View article: Contribution of Hyperconjugation and Inductive Effects to the <i>Pseudo</i> -anomeric Effect in 4-Substituted Methoxycyclohexanes
Contribution of Hyperconjugation and Inductive Effects to the <i>Pseudo</i> -anomeric Effect in 4-Substituted Methoxycyclohexanes Open
The importance of electrostatic nonconventional hydrogen bonds (NCHBs) to the pseudo-anomeric effect of 4-substituted methoxycyclohexanes is evaluated using theory [natural bond orbital (NBO)] to deconvolute electrostatic from other contri…
View article: Identification of Genes Essential for Fluorination and Sulfamylation within the Nucleocidin Gene Clusters of <i>Streptomyces calvus</i> and <i>Streptomyces virens</i>
Identification of Genes Essential for Fluorination and Sulfamylation within the Nucleocidin Gene Clusters of <i>Streptomyces calvus</i> and <i>Streptomyces virens</i> Open
The gene cluster in Streptomyces calvus associated with the biosynthesis of the fluoro‐ and sulfamyl‐metabolite nucleocidin was interrogated by systematic gene knockouts. Out of the 26 gene deletions, most did not affect fluorometabolite p…
View article: Does Perdeuteration Increase the Polarity of Janus Face Cycloalkanes?
Does Perdeuteration Increase the Polarity of Janus Face Cycloalkanes? Open
Stimulated by a suggestion of the late Professor Jack D. Dunitz , that perdeuterated Janus face cycloalkanes may be more polar than their unlabelled forms, the deuterated isotopologue of all cis‐1,2,3,4,5,6‐hexafluorocyclohexane ([ 2 H 6 ]…
View article: 4′-Fluoro-nucleosides and nucleotides: from nucleocidin to an emerging class of therapeutics
4′-Fluoro-nucleosides and nucleotides: from nucleocidin to an emerging class of therapeutics Open
An overview of the history and development of 4′-fluoro-nucleosides as a privileged motif for bioactives is presented.
View article: CCDC 2202379: Experimental Crystal Structure Determination
CCDC 2202379: Experimental Crystal Structure Determination Open
An entry from the Cambridge Structural Database, the world’s repository for small molecule crystal structures. The entry contains experimental data from a crystal diffraction study. The deposited dataset for this entry is freely available …
View article: CCDC 2202380: Experimental Crystal Structure Determination
CCDC 2202380: Experimental Crystal Structure Determination Open
An entry from the Cambridge Structural Database, the world’s repository for small molecule crystal structures. The entry contains experimental data from a crystal diffraction study. The deposited dataset for this entry is freely available …
View article: CCDC 2202377: Experimental Crystal Structure Determination
CCDC 2202377: Experimental Crystal Structure Determination Open
An entry from the Cambridge Structural Database, the world’s repository for small molecule crystal structures. The entry contains experimental data from a crystal diffraction study. The deposited dataset for this entry is freely available …
View article: CCDC 2202382: Experimental Crystal Structure Determination
CCDC 2202382: Experimental Crystal Structure Determination Open
An entry from the Cambridge Structural Database, the world’s repository for small molecule crystal structures. The entry contains experimental data from a crystal diffraction study. The deposited dataset for this entry is freely available …
View article: CCDC 2174309: Experimental Crystal Structure Determination
CCDC 2174309: Experimental Crystal Structure Determination Open
An entry from the Cambridge Structural Database, the world’s repository for small molecule crystal structures. The entry contains experimental data from a crystal diffraction study. The deposited dataset for this entry is freely available …
View article: CCDC 2174307: Experimental Crystal Structure Determination
CCDC 2174307: Experimental Crystal Structure Determination Open
An entry from the Cambridge Structural Database, the world’s repository for small molecule crystal structures. The entry contains experimental data from a crystal diffraction study. The deposited dataset for this entry is freely available …