- Synthesis and nucleic acid binding studies of novel pyrrolidinyl PNA carrying an N-amino-N-methylglycine spacer
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Two novel pyrrolidinyl peptide nucleic acids comprising alternating sequences of thymine-modified D- or L-proline and an N-amino-N-methylglycine spacer were synthesized using solid-phase methodology. UV and CD titrations together with a gel-binding shift assay revealed that neither of the homothymine PNA decamers bind to their complementary DNA or RNA. This was considered to be due to an unfavorable secondary structure which could not be alleviated by the presence of the positively charged protonated amine in the PNA backbone.
- Vilaivan, Tirayut,Suparpprom, Chaturong,Duanglaor, Preeyanut,Harnyuttanakorn, Pongchai,Lowe, Gordon
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- Efficient total synthesis of (+)-negamycin, a potential chemotherapeutic agent for genetic diseases
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Herein, we describe an efficient strategy for the total synthesis of (+)-negamycin using commercially available achiral N-Boc-2-aminoacetaldehyde as starting material with 42% overall yield for a limited number of steps. The Royal Society of Chemistry.
- Hayashi, Yoshio,Regnier, Thomas,Nishiguchi, Shigenobu,Sydnes, Magne O.,Hashimoto, Daisuke,Hasegawa, Junya,Katoh, Takahiro,Kajimoto, Tetsuya,Shiozuka, Masataka,Matsuda, Ryoichi,Node, Manabu,Kiso, Yoshiaki
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supporting information; experimental part
p. 2379 - 2381
(2009/02/03)
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- N- and C-terminal modifications of negamycin
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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).
- 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.
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p. 2413 - 2418
(2007/10/03)
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- Beta-amino acid derivatives useful for the treatment of bacterial infections
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The invention provides compounds that are useful for the treatment of bacterial infections in mammals. More specifically, it is directed to beta-amino acid derivatives or pharmaceutically acceptable salts, prodrugs, or isomers of those compounds that are
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