83436-45-7Relevant articles and documents
N- and C-terminal modifications of negamycin
Raju,Mortell, Kathleen,Anandan, Sampathkumar,O'Dowd, Hardwin,Gao, Hongwu,Gomez, Marcela,Hackbarth, Corinne,Wu, Charlotte,Wang, Wen,Yuan, Zhengyu,White, Richard,Trias, Joaquim,Patel, Dinesh V.
, p. 2413 - 2418 (2007/10/03)
Negamycin 1 is a bactericidal antibiotic with activity against Gram-negative bacteria, and served as a template in an antibiotic discovery program. An orthogonally protected β-amino acid derivative 3a was synthesized and used in parallel synthesis of negamycin derivatives on solid support. This advanced intermediate was also used for N- and C-terminal modifications using solution-phase methodologies. The N-terminal modifications have resulted in the identification of active analogues, whereas the C-terminal modifications resulted in complete loss of antibacterial activity. The N-methyl negamycin analogue, 19a, inhibits protein synthesis (IC50=2.3 μM), has antibacterial activity (Escherichia coli, MIC=16 μg/mL), and is efficacious in an E. coli murine septicemia model (ED50=16.3 mg/kg).
Synthesis of gastrin antagonists, analogues of the C-terminal tetrapeptide of gastrin, by introduction of a β-homo residue
Rodriguez,Fulcrand,Laur,Aumelas,Bali,Martinez
, p. 522 - 528 (2007/10/02)
A series of analogues of Boc-Trp-Leu-Asp-Phe-NH2, a potent gastrin agonist, were synthesized by introducing a β-homo residue in the sequence. These compounds were tested in vivo on acid secretion, in the anesthetized rat, and for their ability
Stereocontrolled Synthesis of (+)-Negamycin from an Acyclic Homoallylamine by 1,3-Asymmetric Induction
Wang, Yi-Fong,Izawa, Toshio,Kobayashi, Susumu,Ohno, Masaji
, p. 6465 - 6466 (2007/10/02)
-
