Sulfur(vi) fluorides as tools in biomolecular and medicinal chemistry

被引:43
作者
Carneiro, Sabrina N. [1 ]
Khasnavis, Samuel R. [1 ]
Lee, Jisun [2 ]
Butler, Todd W. [2 ]
Majmudar, Jaimeen D. [3 ]
Am Ende, Christopher W. [2 ]
Ball, Nicholas D. [1 ]
机构
[1] Pomona Coll, Dept Chem, Claremont, CA 91711 USA
[2] Pfizer Worldwide Res, Dev, Groton, CT 06340 USA
[3] Pfizer Worldwide Res & Dev, Cambridge, MA 02139 USA
基金
美国国家卫生研究院;
关键词
SUFEX CLICK CHEMISTRY; AROMATIC SULFONYL FLUORIDES; PORCINE PANCREATIC ELASTASE; IRREVERSIBLE INHIBITORS; CATHEPSIN-G; REACTIVITY; SITE; FLUOROSULFATE; CHYMOTRYPSIN; CONVENIENT;
D O I
10.1039/d2ob01891h
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
Recent advances in the synthesis of sulfur(vi)-fluorides has enabled incredible growth in their application in biomolecular chemistry. This review aims to serve as a primer highlighting synthetic strategies toward a diversity of S(vi) fluorides and their application in chemical biology, bioconjugation, and medicinal chemistry.
引用
收藏
页码:1356 / 1372
页数:17
相关论文
共 107 条
  • [1] Abbasov ME, 2021, NAT CHEM, V13, P1081, DOI 10.1038/s41557-021-00765-4
  • [2] Potent and Highly Selective Inhibitors of the Proteasome Trypsin-like Site by Incorporation of Basic Side Chain Containing Amino Acid Derived Sulfonyl Fluorides
    Artschwager, Raik
    Ward, David J.
    Gannon, Susan
    Brouwer, Arwin J.
    de Langemheen, Helmus van
    Kowalski, Hubert
    Liskamp, Rob M. J.
    [J]. JOURNAL OF MEDICINAL CHEMISTRY, 2018, 61 (12) : 5395 - 5411
  • [3] Aryl-fluorosulfate-based Lysine Covalent Pan-Inhibitors of Apoptosis Protein (IAP) Antagonists with Cellular Efficacy
    Baggio, Carlo
    Udompholkul, Parima
    Gambini, Luca
    Salem, Ahmed F.
    Jossart, Jennifer
    Perry, J. Jefferson P.
    Pellecchia, Maurizio
    [J]. JOURNAL OF MEDICINAL CHEMISTRY, 2019, 62 (20) : 9188 - 9200
  • [4] BAKER BR, 1971, ANN NY ACAD SCI, V186, P214
  • [5] TISSUE-SPECIFIC IRREVERSIBLE INHIBITORS OF DIHYDROFOLIC REDUCTASE
    BAKER, BR
    [J]. ACCOUNTS OF CHEMICAL RESEARCH, 1969, 2 (05) : 129 - +
  • [6] SPECIFICIC IRREVERSIBLE ENZYME INHIBITORS
    BAKER, BR
    [J]. ANNUAL REVIEW OF PHARMACOLOGY, 1970, 10 : 35 - +
  • [7] Ball N. D., 2020, EMERGING FLUORINATED, V2, P621
  • [8] A Fluorogenic Aryl Fluorosulfate for Intraorganellar Transthyretin Imaging in Living Cells and in Caenorhabditis elegans
    Baranczak, Aleksandra
    Liu, Yu
    Connelly, Stephen
    Du, Wen-Ge Han
    Greiner, Erin R.
    Genereux, Joseph C.
    Wiseman, R. Luke
    Eisele, Yvonne S.
    Bradbury, Nadine C.
    Dong, Jiajia
    Noodleman, Louis
    Sharpless, K. Barry
    Wilson, Ian A.
    Encalada, Sandra E.
    Kelly, Jeffery W.
    [J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2015, 137 (23) : 7404 - 7414
  • [9] The growing applications of SuFEx click chemistry
    Barrow, A. S.
    Smedley, C. J.
    Zheng, Q.
    Li, S.
    Dong, J.
    Moses, J. E.
    [J]. CHEMICAL SOCIETY REVIEWS, 2019, 48 (17) : 4731 - 4758
  • [10] Fluorosulfonyl-substituted xanthines as selective irreversible antagonists for the A1-adenosine receptor
    Beauglehole, AR
    Baker, SP
    Scammells, PJ
    [J]. JOURNAL OF MEDICINAL CHEMISTRY, 2000, 43 (26) : 4973 - 4980