Literature DB >> 17465564

Investigation of the regioselectivity for the staudinger reaction and its application for the synthesis of aminoglycosides with N-1 modification.

Jie Li1, Fang-I Chiang, Hsiao-Nung Chen, Cheng-Wei Tom Chang.   

Abstract

The criteria for controlling the regioselectivity of Staudinger reduction of azides have been investigated. These findings enable a convenient direct N-1 modification of the perazidoneamine and perazidoribostamycin resulting in the synthesis of aminoglycoside antibiotics with activity against drug-resistant bacteria.

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Year:  2007        PMID： 17465564      PMCID： PMC2553255          DOI： 10.1021/jo062588j

Source DB:  PubMed          Journal:  J Org Chem        ISSN： 0022-3263            Impact factor:   4.354


  15 in total

1.  Identification of aminoglycoside-modifying enzymes by susceptibility testing: epidemiology of methicillin-resistant Staphylococcus aureus in Japan.

Authors:  T Ida; R Okamoto; C Shimauchi; T Okubo; A Kuga; M Inoue
Journal:  J Clin Microbiol       Date:  2001-09       Impact factor: 5.948

2.  Tuning the regioselectivity of the Staudinger reaction for the facile synthesis of kanamycin and neomycin class antibiotics with N-1 modification.

Authors:  Jie Li; Hsiao-Nung Chen; Huiwen Chang; Jinhua Wang; Cheng-Wei Tom Chang
Journal:  Org Lett       Date:  2005-07-07       Impact factor: 6.005

3.  Overexpression and characterization of the chromosomal aminoglycoside 6'-N-acetyltransferase from Enterococcus faecium.

Authors:  G D Wright; P Ladak
Journal:  Antimicrob Agents Chemother       Date:  1997-05       Impact factor: 5.191

4.  Biological transformation of kanamycin A to amikacin (BBK-8).

Authors:  L M Cappelletti; R Spagnoli
Journal:  J Antibiot (Tokyo)       Date:  1983-03       Impact factor: 2.649

5.  Chemical modification of 5,3',4'-trideoxykanamycin B.

Authors:  H Umezawa; T Miyasaka; H Iwasawa; D Ikeda; S Kondo
Journal:  J Antibiot (Tokyo)       Date:  1981-12       Impact factor: 2.649

6.  Aminoglycoside antibiotics. 5. Regiospecific synthesis of 1-N-[(S)-4-amino-2-hydroxybutyryl]-2"-deoxykanamycin B from neamine.

Authors:  M N Sharma; V Kumar; W A Remers
Journal:  J Antibiot (Tokyo)       Date:  1982-07       Impact factor: 2.649

7.  Characterization of the extended-spectrum beta-lactamase reference strain, Klebsiella pneumoniae K6 (ATCC 700603), which produces the novel enzyme SHV-18.

Authors:  J K Rasheed; G J Anderson; H Yigit; A M Queenan; A Doménech-Sánchez; J M Swenson; J W Biddle; M J Ferraro; G A Jacoby; F C Tenover
Journal:  Antimicrob Agents Chemother       Date:  2000-09       Impact factor: 5.191

8.  Sequence and characterization of a novel chromosomal aminoglycoside phosphotransferase gene, aph (3')-IIb, in Pseudomonas aeruginosa.

Authors:  H Hächler; P Santanam; F H Kayser
Journal:  Antimicrob Agents Chemother       Date:  1996-05       Impact factor: 5.191

9.  Conformational Studies in the Cyclohexane Series. 1. Experimental and Computational Investigation of Methyl, Ethyl, Isopropyl, and tert-Butylcyclohexanes.

Authors:  Kenneth B. Wiberg; Jack D. Hammer; Henry Castejon; William F. Bailey; Eric L. DeLeon; Ronald M. Jarret
Journal:  J Org Chem       Date:  1999-03-19       Impact factor: 4.354

10.  Synthesis of 5-deoxy-5-epifluoro derivatives of arbekacin, amikacin, and 1-N-[(S)-4-amino-2-hydroxybutanoyl]tobramycin (study on structure--toxicity relationships).

Authors:  T Shitara; E Umemura; T Tsuchiya; T Matsuno
Journal:  Carbohydr Res       Date:  1995-10-16       Impact factor: 2.104
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  6 in total

1.  A review of patents (2011-2015) towards combating resistance to and toxicity of aminoglycosides.

Authors:  Nishad Thamban Chandrika; Sylvie Garneau-Tsodikova
Journal:  Medchemcomm       Date:  2015-11-19       Impact factor: 3.597

2.  Antifungal Amphiphilic Aminoglycosides.

Authors:  C-W T Chang; J Y Takemoto
Journal:  Medchemcomm       Date:  2014-08-01       Impact factor: 3.597

3.  Surprising alteration of antibacterial activity of 5"-modified neomycin against resistant bacteria.

Authors:  Jianjun Zhang; Fang-I Chiang; Long Wu; Przemyslaw Greg Czyryca; Ding Li; Cheng-Wei Tom Chang
Journal:  J Med Chem       Date:  2008-12-11       Impact factor: 7.446

Review 4.  Antifungal amphiphilic kanamycins: new life for an old drug.

Authors:  Yagya Prasad Subedi; Madher N AlFindee; Jon Y Takemoto; Cheng-Wei Tom Chang
Journal:  Medchemcomm       Date:  2018-04-17       Impact factor: 3.597

5.  Late-Stage Modification of Aminoglycoside Antibiotics Overcomes Bacterial Resistance Mediated by APH(3') Kinases.

Authors:  Andreas A Bastian; Maria Bastian; Manuel Jäger; Mark Loznik; Eliza M Warszawik; Xintong Yang; Nabil Tahiri; Peter Fodran; Martin D Witte; Anne Thoma; Jens Köhler; Adriaan J Minnaard; Andreas Herrmann
Journal:  Chemistry       Date:  2022-05-17       Impact factor: 5.020

6.  Synthesis and combinational antibacterial study of 5''-modified neomycin.

Authors:  Jianjun Zhang; Katherine Keller; Jon Y Takemoto; Mekki Bensaci; Anthony Litke; Przemyslaw Greg Czyryca; Cheng-Wei Tom Chang
Journal:  J Antibiot (Tokyo)       Date:  2009-07-24       Impact factor: 2.649
  6 in total

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