156699-39-7Relevant articles and documents
Total synthesis and structure elucidation of JBIR-39: A linear hexapeptide possessing piperazic acid and γ-hydroxypiperazic acid residues
Yoshida, Masahito,Sekioka, Naoki,Izumikawa, Miho,Kozone, Ikuko,Takagi, Motoki,Shin-ya, Kazuo,Doi, Takayuki
supporting information, p. 3031 - 3041 (2015/02/05)
The total synthesis and stereochemical structural elucidation of JBIR-39, containing four nonproteinogenic piperazic acid (Piz) residues, is reported. The synthesis includes Sc(OTf)3-catalyzed acylation of a Piz(γ-OTBS) derivative with piperazi
Synthesis of the tripeptide domain of sanglifehrins using asymmetric phase-transfer catalysis
White, James D.,Suttisintong, Khomson
, p. 2757 - 2762 (2013/04/23)
The tripeptide (S)-valinyl-(S)-m-hydroxyphenylalanyl-(3S)-piperazate common to immunosuppressant sanglifehrins was synthesized from the constituent amino acid residues in nine steps and 42% overall yield. A key construction was the installation of (S) absolute configuration in m-hydroxyphenylalanine using asymmetric phase-transfer catalysis in the presence of N-(1-naphthyl) cinchonidinium bromide. Cbz-protected (S)-valine was first coupled to the amino group of (S)-m-triisopropylsilyloxyphenylalanine tert-butyl ester, and the resulting dipeptide after ester cleavage was linked to (3S)-methyl piperazate.
Stereochemical Definition and Chirospecific Synthesis of the Peptide Deformylase Inhibitor Sch 382583
Coats, Reed A.,Lee, Sheng-Lian,Davis, Kari A.,Patel, Kanu M.,Rhoads, Elaine K.,Howard, Michael H.
, p. 1734 - 1737 (2007/10/03)
The recently reported natural product Sch 382583 (1), an inhibitor of peptide deformylase, has been synthesized in 16 steps from commercially available starting materials. The three chiral centers were set by a combination of chiral auxiliary and chiral p