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A sulfilimine (sulfimide) is a type of chemical compound containing a sulfur to nitrogen double bond. The parent compound is sulfilimine H2S=NH, which is mainly of theoretical interest. Other simple examples are methylphenylsulfoximine and S,S-diphenylsulfilimine:
Sulfilimine bonds in proteins
Sulfilimine bonds stabilize collagen IV strands found in the extracellular matrix. These bonds covalently connect hydroxylysine and methionine residues of adjacent polypeptide strands to form a larger collagen trimer.
References
- The preparation and structure of novel sulfimide systems; X-ray crystal structures of 1,4-(PhS{NH})2C6H4(and dihydrate), 1,2-(PhS{NH})(PhS)C6H4·H2O and of and its hydrate Mark R. J. Elsegood, Kathryn E. Holmes, Paul F. Kelly, Jonathan Parr and Julia M. Stonehouse New J. Chem., 2002, 26, 202 - 206. doi:10.1039/b103502a
- sigmaaldrich.com/catalog methyl-phenylsulfoximine
- sigmaaldrich.com/catalog S,S-diphenylsulfilimine
- Vanacore R, Ham AL, Voehler M, Sanders CR, Conrads TP, Veenstra TD, Sharpless KB, Dawson PE, Hudson BG (September 4, 2009). "A sulfilimine bond identified in collagen IV". Science. 325 (5945): 1230–1234. Bibcode:2009Sci...325.1230V. doi:10.1126/science.1176811. PMC 2876822. PMID 19729652.
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