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Chemical Structure| 5029-67-4 Chemical Structure| 5029-67-4
Chemical Structure| 5029-67-4

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CAS No.: 5029-67-4

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Synonyms: 2-Pyridyl iodide

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Jacob Silzel ; Chengwei Chen ; Colomba Sanchez-Marsetti ; Phillip Farias ; Veronica Carta ; W. Hill Harman , et al.

Abstract: Cysteine is the most reactive naturally occurring amino acid due to the presence of a free thiol, presenting a tantalizing handle for covalent modification of peptides/proteins. Although many mass spectrometry experiments could benefit from site-specific modification of Cys, the utility of direct arylation has not been thoroughly explored. Recently, Spokoyny and coworkers reported a Au(III) organometallic reagent that robustly arylates Cys and tolerates a wide variety of solvents and conditions. Given the chromophoric nature of aryl groups and the known susceptibility of carbon-sulfur bonds to photodissociation, we set out to identify an aryl group that could efficiently cleave Cys carbon-sulfur bonds at 266 nm. A streamlined workflow was developed to facilitate rapid examination of a large number of aryls with minimal sample using a simple test peptide, RAAACGVLK. We were able to identify several aryl groups that yield abundant homolytic photodissociation of the adjacent Cys carbon-sulfur bonds with short activation times (<10 ms). In addition, we characterized the radical products created by photodissociation by subjecting the product ions to further collisional activation. Finally, we tested Cys arylation with human hemoglobin, identified reaction conditions that facilitate efficient modification of intact proteins, and evaluated the photochemistry and activation of these large radical ions.

Keywords: Fragmentation ; photodissociation ; radical-directed dissociation ; cysteine modification

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Product Details of 2-Iodopyridine

CAS No. :5029-67-4
Formula : C5H4IN
M.W : 205.00
SMILES Code : IC1=NC=CC=C1
Synonyms :
2-Pyridyl iodide
MDL No. :MFCD00464928
InChI Key :CCZWSTFVHJPCEM-UHFFFAOYSA-N
Pubchem ID :221126

Safety of 2-Iodopyridine

GHS Pictogram:
Signal Word:Warning
Hazard Statements:H315-H319-H335
Precautionary Statements:P261-P305+P351+P338

Application In Synthesis of 2-Iodopyridine

* 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.

  • Upstream synthesis route of [ 5029-67-4 ]
  • Downstream synthetic route of [ 5029-67-4 ]

[ 5029-67-4 ] Synthesis Path-Upstream   1~1

  • 1
  • [ 5029-67-4 ]
  • [ 927-74-2 ]
  • [ 395652-44-5 ]
YieldReaction ConditionsOperation in experiment
67% With potassium phosphate In water; isopropyl alcohol at 80℃; for 20 h; Sealed tube General procedure: In a sealed tube, aryl iodide (1 mmol, 1 equiv.), K3PO4(2 mmol,2 equiv.), catalyst (2 molpercent Pd) were suspended in i-PrOH (3 mL)and H2O (3 mL). The acetylene derivative (1.2 mmol, 1.2 equiv.)was added and the resulting mixture was stirred at 80C for 20 h.After cooling to room temperature, EtOAc (20 mL) and H2O (20 mL)were added and the mixture was filtered over a pad of Celite?.The aqueous layer was extracted twice with EtOAc (2 × 20 mL). Thecollected organics extracts were washed by brine (60 mL), driedon MgSO4, filtered and concentrated under reduced pressure. Thecrude product was purified by flash chromatography.
References: [1] Applied Catalysis A: General, 2014, vol. 482, p. 157 - 162.
 

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