Secondary Amine Binary Coding

The tags are a set of relatively hydrophobic amines, such as HN(Et)(Bu), HNMe(C6Hu), HNBu2, HNMe(C7H]5), HN[CH2CH(Et)C4H9]2. The set is selected to ensure reliable separation of the dansyl derivatives of the amines by reversed-phase HPLC. The tagging monomer units are synthesized by reaction of an N-protected iminodiacetic anhydride with a secondary amine from the set (Fig. 7). 

Secondary amine encoding method was used in the synthesis of a library of pyrrolidine-based inhibitors of angiotensin converting enzyme (ACE) via 2 + 3 cycloaddition [29]. 

---

Figure 6. Resin construct for secondary amine binary coding [26, 27].

Ni, Z.-J., Maclean, D., Holmes, C.P., and Gallop, M.M. Encoded Combinatorial Chemistry Binary Coding Using Chemically Robust Secondary Amine Tags. In Methods in Enzymology, vol. 267, Combinatorial Chemistry. Abelson, J.N. (ed.). Academic Press San Diego pp. 261-272 (1996). 

Z. J. Ni, D. Maclean, C. P. Holmes, M. A. Gallop, Encoded combinatorial chemistry binary coding using chemically robust secondary amine tags. Methods Enzymol 1996, 267, 261-272. 

---