After the reaction of lysozyme C and one equivalent of 3b, the major component shown in the mass spectrum is represented by remains of the non-modified lysozyme C with a mass of 14306 Da (Figure ). A second peak was observed with approximately 40% intensity and a mass of 14458 Da. The mass difference of ∆ = 152 Da corresponds to the addition of one molecule 3b (Figure ), which confirms the successful modification of our model protein. When one equivalent of both 3b and NMM is used to favor the double modification of lysozyme C, a different mass peak appears (Figure ). The peak with an approximate intensity of 13% and a mass of 14586 Da corresponds to a mass difference of ∆ = 281 Da and can be assigned to a modified species that underwent exactly one double modification. At the presented stoichiometric ratios, no higher degrees of substitution were observed within the 24 h reaction time, yet the overall conversions remain limited. To reach higher conversions, each respective modification reaction was attempted using higher quantities of 3b and NMM (10, 20, 30 and 50 eq, Table -13, Figure -85). Using excess of the reagents resulted in higher conversions but also higher degrees of substitution, with mono-di-triand tetra-substituted products. Overall, the reaction conditions can be adjusted depending on the needs of a given system and therefore 3b shows good potential to be used as chemical anchor and/or ligation chemistry to combine synthetic and biological building blocks. Further implementations of this ligation strategy into polymeric systems to enable the facile synthesis of biohybrid materials are ongoing.