1032313-52-2Relevant academic research and scientific papers
Synthesis of non-natural aromatic α-amino acids by a Heck reaction
Suhartono, Marcel,Weidlich, Markus,Stein, Torsten,Karas, Michael,Duerner, Gerd,Goebel, Michael W.
experimental part, p. 1608 - 1614 (2009/04/11)
Alkene 3, a TBS- and Cbz-protected derivative of vinylglycinol, safely available from methionine, undergoes efficient Heck coupling reactions in high yields. The resulting products can be converted into enantiopure α-amino acids with aromatic and heteroaromatic side-chains. Compound 6a, a brightly fluorescent Fmoc-protected pyrene amino acid is of special interest. Tripeptide 8a, composed of this building block and two arginines, binds to TAR, an RNA element regulating transcriptional efficiency in HIV, with a Kd value of 50 nM. This compound also inhibits a coupled cell-free transcription- translation assay (IC50 = 40 μM) and shows pronounced antibacterial activity against B. subtilis. Wiley-VCH Verlag GmbH & Co. KGaA, 2008.
