Cell-surface ketones

J. Kevin, L. K. Yarema, R. E. Mahal, E. C. Bruehl, and C. R. Bertozzi, Metabolic delivery of ketone groups to sialic acid residues. Application to cell surface glycoform engineering, J. Biol. Chem., 273 (1998) 31168-31179. 

Hang HC, Bertozzi CR. Ketone isoteres of 2-V-acetamido-sugars as substrates for metabolic cell surface engineering. J. Am. Chem. Soc. 2001 123 1242-1243. 

Ketone-based chemoselective ligation reactions that exploit cell surface displayed SiaSLev (32)... 

The ketone-based chemoselective ligation reactions described above initially demonstrated the versatility and potential of MOE to modulate biology through changes in cell surface... 

Fig. 10.3-16 Introduction of unnatural functional groups through posttranslational modification, (a) Ketones and azides can be introduced onto cell surfaces by feeding cells with unnatural sialic acid precursors, such as mannosamine derivatives 40b and c. These are incorporated into cell-surface glycans, which can be further elaborated using additional bioconjugation reactions, (b) Specific amino acid sequences can be modified using biotin ligase. Interestingly, ketobiotin" is also recognized as a substrate for the enzyme, allowing a...

One way to modify the cell-surface molecules is by introducing nonnatural monosugars into the biosynthetic pathways that build up polysaccharides (Figure 46.3) [15,16]. By introducing monosaccharides with synthetic ketone groups, Bertozzi et al. were able to engineer previously nonadherent Jurkat cells to adhere to hpid bilayers decorated with azides [17]. These researchers have also demonstrated that a... 

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