Solution- and solid-phase synthesis of triazole oligomers that display protein-like functionality.
We recently developed a new class of oligomers that contain alpha-amino acid residues linked by 1,2,3-triazole groups [Angelo, N. G.; Arora, P. S. J. Am. Chem. Soc. 2005, 127, 17134-17135]. Synthesis of these oligomers involves an iterative sequence consisting of diazotransfer and Huisgen 1,3-dipolar cycloaddition steps. In this contribution, we describe an efficient one-pot, two-step sequence for the preparation of triazoles from the corresponding amino acid-derived amines and alkynes in solution. The one-pot sequence affords the desired products in significantly higher yields than our original method. We also outline a highly effective protocol for the synthesis of these triazole-based biomimetic oligomers on the solid phase. We find that amino acid derivatives and iterative formation of triazole rings require nontraditional reaction conditions for high yields.
Angelo
Nicholas G
NG
Department of Chemistry, New York University, New York, New York 10003, USA.
Arora
Paramjit S
PS
D000480:Alkynes / Q000737:chemistry*; D000596:Amino Acids / Q000737:chemistry*; D040761:Biomimetic Materials / Q000737:chemistry*; D002384:Catalysis; D003500:Cyclization; D044367:Phase Transition; D011506:Proteins / Q000737:chemistry*; D012996:Solutions; D014230:Triazoles / Q000138:chemical synthesis* / Q000737:chemistry
D000480:Alkynes; D000596:Amino Acids; D011506:Proteins; D012996:Solutions; D014230:Triazoles