138774-95-5Relevant academic research and scientific papers
Total synthesis of hytramycin V, an antibiotic cyclopeptide
Igarashi, Masayuki,Inaba, Tetsuya,Ishizaki, Yoshimasa,Kigoshi, Hideo,Yoshida, Masahito
supporting information, p. 1922 - 1930 (2021/08/13)
The total synthesis of the piperazic acid-containing antibiotic cyclic peptide, hytramycin V, has been achieved. Unexpected cleavage of the peptide bond was observed during the synthesis of a pentapeptide, we then successfully found that the addition of 2,6-di-tert-butylpyridine (2,6-DTBP) was effective to prevent the cleavage upon acylation with AgCN, leading to a pentapeptide in excellent yield. The synthesis of a hexapeptide, followed by global deprotection of the protecting groups provided a cyclization precursor. Finally, macrolactamization of the precursor using T3Pμ under high-dilution conditions furnished the desired natural product, hytramycin V. The synthesis of the enantiomer of hytramycin V was also achieved, and no difference between the enantiomers was observed in the evaluation of their antibacterial activity against Mycobacterium strains, revealing the fact that the potency of the activity was not dependent on the chirality of the cyclopeptide backbone.
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
, 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
