Fmoc-Lys(Biotin)-OH [146987-10-2]

N-alpha-Fmoc-N-epsilon-biotinyl-L-lysine

Molecular Weight: 594.7

Fmoc-Lys(Biotin)-OH solubility is better in NMP than DMF. A 0.1 M solution in NMP can be prepared with heating at 40 C. Recently, a 2:1 (v/v) mixture of DCM and NMP has been utilized to dissolve this product (K. Hartman, P. Mielczarek, J. Silberg, Molecules, 2020, 26(4), 813). Fmoc-Lys(Biotin)-OH has low solubility in DMF, but is soluble in a mixture of DMF and DIPEA.  75 mg of Fmoc-Lys(Biotin) is soluble in 1 ml of DMF containing 80 microliters of DIPEA (di-iso-propylethylamine). This may be most helpful with HBTU, HATU, or HCTU      coupling reagents where DIPEA is usually added in the coupling mixture.

Fmoc-Lys(Biotin)-OH is useful for preparing specifically labeled peptides to use as probes. The biotinylated peptides are detected using labeled avidin or streptavidin which tightly bind to biotin. Because labeled avidin or streptavidin are labeled in multiple sites, the binding of labeled avidin to a biotinylated probe produces an amplified response compared to the direct incorporation of the label into the peptide. Biotinylation can modify the activity of a peptide. Recently, biotinylation of lysine residues in exendin-4 was reported to improve the hypoglycimic effects of the peptide. Significantly, incorporation of Lys(biotin) led to an product that could be taken orally. (Jin, C.H., et al. J. Control Release 2009, 133, 172.)