Publication Cover
Synthetic Communications
An International Journal for Rapid Communication of Synthetic Organic Chemistry
Volume 36, 2006 - Issue 4
100
Views
6
CrossRef citations to date
0
Altmetric
Original Articles

Hydroxyl Substitution Studies at the 5″‐Position in the Neomycin B Series: Introduction of a Phtalimide Group Under Mitsunobu Reaction Conditions

, , &
Pages 487-493 | Received 26 Jun 2005, Published online: 19 Aug 2006

References

  • Moazed , D. and Noller , H. F. 1991 . Interaction of antibiotics with functional sites in 16S ribosomal RNA . Nature , 327 : 389 – 394 .
  • Woodcock , J. , Moazed , D. , Cannon , M. , Davies , J. and Noller , H. F. 1991 . Interaction of antibiotics with A‐ and P‐site‐specific bases in 16S ribosomal RNA . EMBO J. , 10 : 3099 – 3103 .
  • Magnet , S. and Blanchard , J. S. 2005 . Molecular insights into aminoglycoside action and resistance . Chem. Rev. , 105 : 477 – 497 .
  • Fourmy , D. , Recht , M. I. , Blanchard , S. C. and Puglisi , J. D. 1996 . Structure of the A site of Escherichia coli 16S ribosomal RNA complexed with an aminoglycoside antibiotic . Science , 274 : 1367 – 1371 .
  • Carter , A. P. , Clemons , W. M. , Brodersen , D. E. , Morgan‐Warren , R. J. , Wimberly , B. T. and Ramakrishnan , V. 2000 . Functional insights from the structure of the 30S ribosomal subunit and its interactions with antibiotics . Nature , 407 : 340 – 348 .
  • Vicens , Q. and Westhof , E. 2001 . Crystal structure of paromomycin docked into the eubacterial ribosomal decoding A site . Structure (Camb.) , 9 : 647 – 658 .
  • Wong , C.‐H. 1983 . A library approach to the discovery of small molecules that recognize RNA: Use of a 1,3‐hydroxyamine motif as core . J. Am. Chem. Soc. , 120 : 8319 – 8327 .
  • Griffey , R. H. , Hofstadler , S. A. , Sannes‐Lowery , K. A. , Ecker , D. J. and Crooke , S. T. 1999 . Determinants of aminoglycoside‐binding specificity for rRNA by using mass spectrometry . Proc. Natl. Acad. Sci. USA , 96 : 10129 – 10133 .
  • Botto , R. E. and Coxon , B. 1998 . Nitrogen‐15 nuclear magnetic resonance spectroscopy of neomycin B and related aminoglycosides . J. Am. Chem. Soc. , 105 : 1021 – 1028 .
  • Hanessian , S. , Massé , R. and Capmeau , M.‐L. 1977 . Aminoglycoside antibiotics: Synthesis of 5″‐amino‐5″‐deoxyneomycin and 5″‐amino‐5″‐deoxyparomomycin . J. Antibiot. , 30 : 893 – 896 .
  • Wang , H. and Tor , Y. 1998 . RNA‐aminoglycoside interactions: Design, synthesis, and binding of amino‐glycosides to RNA . Angew. Chem. Int. Ed. , 37 : 109 – 111 .
  • Boer , J. , Blount , K. F. , Luedtke , N. W. , Elson‐Schwab , L. and Tor , Y. 2005 . RNA‐selective modification by a platinum(II) complex conjugated to amino‐ and guanidinoglycosides . Angew. Chem. Int. Ed. , 44 : 927 – 932 .
  • Xue , L. , Charles , I. and Arya , D. P. 2002 . Pyrene‐neomycin conjugate: Dual recognition of a DNA triple helix . J. Chem. Soc., Chem. Commun. , : 70 – 71 .
  • Hughes , D. L. 1992 . The Mitsunobu reaction . Org. React. , 42 : 335 – 656 .
  • Michael , K. , Wang , H. and Tor , Y. 1999 . Enhanced RNA binding of dimerized aminoglycosides . Bioorg. Med. Chem. , 7 : 1361 – 1371 .
  • Göksu , S. , Seçen , H. and Sütbeyaz , Y. 2002 . One‐pot and stereospecific synthesis of cis‐1,2‐diazides via Mitsunobu reaction of epoxides . Synthesis , 65 : 2373 – 2378 .
  • Hernandez Linares , A. , Fourmy , D. , Fourrrey , J.‐L. and Loukaci , A. 2005 . Introduction of a substituent at the 5″‐position of N‐Boc neomycin B under Mitsunobu reaction conditions . Org. Biomol. Chem. , 3 : 2064 – 2066 .
  • Note added in proof: Following a personal communication with Professor I. D. Jenkins structures 8 and 9 should be revised as β‐3‴, 4‴‐epoxides (Quader, S. et al. Mitsunobu dehydration of N‐Boc neomycin B, Org. Biomol. Chem., in the press). We thank Dr. M.‐T. Martin (ICSN) for a correct reinterpretation of the NMR data

Reprints and Corporate Permissions

Please note: Selecting permissions does not provide access to the full text of the article, please see our help page How do I view content?

To request a reprint or corporate permissions for this article, please click on the relevant link below:

Academic Permissions

Please note: Selecting permissions does not provide access to the full text of the article, please see our help page How do I view content?

Obtain permissions instantly via Rightslink by clicking on the button below:

If you are unable to obtain permissions via Rightslink, please complete and submit this Permissions form. For more information, please visit our Permissions help page.