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[ CAS No. 289-80-5 ] {[proInfo.proName]}

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Chemical Structure| 289-80-5
Chemical Structure| 289-80-5
Structure of 289-80-5 * Storage: {[proInfo.prStorage]}

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Product Citations

Product Citations      Expand+

Anushree Mondal ; Pronay Roy ; Jaclyn Carrannatto , et al. DOI: PubMed ID:

Abstract: The prenylated-flavin mononucleotide-dependent decarboxylases (also known as UbiD-like enzymes) are the most recently discovered family of decarboxylases. The modified flavin facilitates the decarboxylation of unsaturated carboxylic acids through a novel mechanism involving 1,3-dipolar cyclo-addition chemistry. UbiD-like enzymes have attracted considerable interest for biocatalysis applications due to their ability to catalyse (de)carboxylation reactions on a broad range of aromatic substrates at otherwise unreactive carbon centres. There are now ～35[thin space (1/6-em)]000 protein sequences annotated as hypothetical UbiD-like enzymes. Sequence similarity network analyses of the UbiD protein family suggests that there are likely dozens of distinct decarboxylase enzymes represented within this family. Furthermore, many of the enzymes so far characterized can decarboxylate a broad range of substrates. Here we describe a strategy to identify potential substrates of UbiD-like enzymes based on detecting enzyme-catalysed solvent deuterium exchange into potential substrates. Using ferulic acid decarboxylase (FDC) as a model system, we tested a diverse range of aromatic and heterocyclic molecules for their ability to undergo enzyme-catalysed H/D exchange in deuterated buffer. We found that FDC catalyses H/D exchange, albeit at generally very low levels, into a wide range of small, aromatic molecules that have little resemblance to its physiological substrate. In contrast, the sub-set of aromatic carboxylic acids that are substrates for FDC-catalysed decarboxylation is much smaller. We discuss the implications of these findings for screening uncharacterized UbiD-like enzymes for novel (de)carboxylase activity.

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Matthew T. Fortunato ; Curtis E. Moore ; Claudia Turro DOI: PubMed ID:

Abstract: A new series of Rh2(II,II) complexes with the formula cis-[Rh2(DTolF)2(bpnp)(L)]2+, where bpnp = 2,7-bis(2-pyridyl)-1,8-naphthyridine, DTolF = N,N′-di(p-tolyl) formamidinate, and L = pdz (pyridazine; 2), cinn (cinnoline; 3), and bncn (benzo[c]cinnoline; 4), were synthesized from the precursor cis-[Rh2(DTolF)2(bpnp)(CH3CN)2]2+ (1). The first reduction couple in 2–4 is localized on the bpnp ligand at approximately ?0.52 V vs Ag/AgCl in CH3CN (0.1 M TBAPF6), followed by reduction of the corresponding diazine ligand. Complex 1 exhibits a Rh2(δ*)/DTolF → bpnp(π*) metal/ligand-to-ligand charge-transfer (1ML-LCT) absorption with a maximum at 767 nm (ε = 1800 M–1 cm–1). This transition is also present in the spectra of 2–4, overlaid with the Rh2(δ*)/DTolF → L(π*) 1ML-LCT bands at 516 nm in 2 (L = pdz), 640 nm in 3 (L = cinn), and 721 nm in 4 (L = bncn). Complexes 2 and 3 exhibit Rh2(δ*)/DTolF → bpnp 3ML-LCT excited states with lifetimes, τ, of 3 and 5 ns, respectively, in CH3CN, whereas the lowest energy 3ML-LCT state in 4 is Rh2(δ*)/DTolF → bncn in nature with τ = 1 ns. Irradiation of 4 with 670 nm light in DMF in the presence of 0.1 M TsOH (p-toluene sulfonic acid) and 30 mM BNAH (1-benzyl-1,4-dihydronicotinamide) results in the production of H2 with a turnover number (TON) of 16 over 24 h. The axial capping of the Rh2(II,II) bimetallic core with the bpnp ligand prevents the formation of an Rh–H hydride intermediate. These results show that the observed photocatalytic reactivity is localized on the bncn ligand, representing the first example of ligand-centered H2 production.

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Product Details of [ 289-80-5 ]

CAS No. :289-80-5 MDL No. :MFCD00006463
Formula : C4H4N2 Boiling Point : No data available
Linear Structure Formula :- InChI Key :PBMFSQRYOILNGV-UHFFFAOYSA-N
M.W : 80.09 Pubchem ID :9259
Synonyms :

Calculated chemistry of [ 289-80-5 ]      Expand+

Physicochemical Properties

Num. heavy atoms : 6
Num. arom. heavy atoms : 6
Fraction Csp3 : 0.0
Num. rotatable bonds : 0
Num. H-bond acceptors : 2.0
Num. H-bond donors : 0.0
Molar Refractivity : 22.03
TPSA : 25.78 ?2

Pharmacokinetics

GI absorption : High
BBB permeant : No
P-gp substrate : No
CYP1A2 inhibitor : No
CYP2C19 inhibitor : No
CYP2C9 inhibitor : No
CYP2D6 inhibitor : No
CYP3A4 inhibitor : No
Log Kp (skin permeation) : -7.3 cm/s

Lipophilicity

Log Po/w (iLOGP) : 1.02
Log Po/w (XLOGP3) : -0.72
Log Po/w (WLOGP) : 0.48
Log Po/w (MLOGP) : -0.11
Log Po/w (SILICOS-IT) : 1.19
Consensus Log Po/w : 0.37

Druglikeness

Lipinski : 0.0
Ghose : None
Veber : 0.0
Egan : 0.0
Muegge : 2.0
Bioavailability Score : 0.55

Water Solubility

Log S (ESOL) : -0.62
Solubility : 19.1 mg/ml ; 0.238 mol/l
Class : Very soluble
Log S (Ali) : 0.65
Solubility : 362.0 mg/ml ; 4.51 mol/l
Class : Highly soluble
Log S (SILICOS-IT) : -1.53
Solubility : 2.35 mg/ml ; 0.0293 mol/l
Class : Soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 0.0 alert
Leadlikeness : 1.0
Synthetic accessibility : 1.0

Safety of [ 289-80-5 ]

Signal Word:Warning Class:
Precautionary Statements:P261-P305+P351+P338-P210 UN#:
Hazard Statements:H315-H319-H335-H227 Packing Group:
GHS Pictogram:

Application In Synthesis of [ 289-80-5 ]

* All experimental methods are cited from the reference, please refer to the original source for details. We do not guarantee the accuracy of the content in the reference.

  • Downstream synthetic route of [ 289-80-5 ]

[ 289-80-5 ] Synthesis Path-Downstream   1~2

  • 1
  • [ 1120-95-2 ]
  • [ 289-80-5 ]
YieldReaction ConditionsOperation in experiment
With potassium acetate; palladium diacetate; bis(pinacol)diborane; tricyclohexylphosphine; In 1,4-dioxane; at 110℃; for 0.166667h;Inert atmosphere; General procedure: The Miyaura borylation reactions were carried out as follows: Chloropyrazines (3.0 mmol), B2pin2 (838 mg, 3.3 mmol), Pd(OAc)2 (14 mg, 2 mol percent), PCy3 (34 mg, 4 mol percent) and AcOK (750 mg, 7.5 mmol) was added in a 50 ml three necked flask fitted with a condenser, and dioxane (15 ml) was added at last. Then the reaction mixture was stirred at a preheated oil bath 110 oC under nitrogen atmosphere for 10 min. After complete completion of starting material checked by TLC, the reaction was cooled to room temperature, EtOAc (20 ml) was added. After filtration through Celite ? and concentration under vacuo, the resulting residue was precipitated from n-hexane:Et2O to afford corresponding boronic esters.
  • 2
  • [ 1120-95-2 ]
  • [ 10034-85-2 ]
  • red phosphorus [ No CAS ]
  • [ 289-80-5 ]
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