4-Vinylpyridine

4-Vinylpyridine

4-Vinylpyridine

Chemical compound

4-Vinylpyridine (4-VP) is an organic compound with the formula CH2CHC5H4N. It is a derivative of pyridine with a vinyl group in the 4-position. It is a colorless liquid, although impure samples are often brown. It is a monomeric precursor to specialty polymers. 4-Vinylpyridine is prepared by the condensation of 4-methylpyridine and formaldehyde.[1]

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4-VP is sometimes used in biochemistry to alkylate protein cysteine residues. When compared to other alkylation agents, such as iodoacetamide, acrylamide, and N-ethylmaleimide, 4-VP is less reactive, meaning the completion rate of cysteine alkylation is lower, but it also yields fewer side reactions.[2] For some uses, such as during mass spectrometry measurements, 4-VP might be better because it is basic and can thus be protonated, adding net charge.[3]

See also

References

  1. [1]
    Shimizu, Shinkichi; Watanabe, Nanao; Kataoka, Toshiaki; Shoji, Takayuki; Abe, Nobuyuki; Morishita, Sinji; Ichimura, Hisao (2007). "Pyridine and Pyridine Derivatives". Ullmann's Encyclopedia of Industrial Chemistry. Weinheim: Wiley-VCH. doi:10.1002/14356007.a22_399. ISBN 978-3527306732.
  2. [2]
    Suttapitugsakul, Suttipong; Xiao, Haopeng; Smeekens, Johanna; Wu, Ronghu (2017). "Evaluation and optimization of reduction and alkylation methods to maximize peptide identification with MS-based proteomics". Molecular BioSystems. 13 (12): 2574–2582. doi:10.1039/C7MB00393E. ISSN 1742-206X. PMC 5698164. PMID 29019370.
  3. [3]
    Sechi, Salvatore; Chait, Brian T. (1998-12-01). "Modification of Cysteine Residues by Alkylation. A Tool in Peptide Mapping and Protein Identification". Analytical Chemistry. 70 (24): 5150–5158. doi:10.1021/ac9806005. ISSN 0003-2700. PMID 9868912.
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