Publication Cover
Synthetic Communications
An International Journal for Rapid Communication of Synthetic Organic Chemistry
Volume 39, 2009 - Issue 19
156
Views
4
CrossRef citations to date
0
Altmetric
Original Articles

Efficient Synthesis of N-Fmoc-Aminoalkoxy Pentafluorophenyl Carbonates: Application for the Synthesis of Oligopeptidyl Carbamates

&
Pages 3555-3566 | Received 31 Oct 2008, Published online: 04 Sep 2009

REFERENCES

  • Cho , C. Y. ; Moran , E. J. ; Cherry , S. R. ; Stephans , J. C. ; Fodor , S. P. A. ; Adams , C. L. ; Sundaram , A. ; Jacobs , J. W. ; Schultz , P. G. An unnatural biopolymer . Science 1993 , 261 , 1303 – 1305 .
  • Wilson , M. E. ; Nowick , J. S. In Methods of Organic Chemistry: Synthesis of Peptides and Peptidomimetics ; Houben-Weyl : New York , 2003 , vol. E22c , pp. 590 – 605 .
  • Gordon , E. M. ; Barrett , R. W. ; Dower , W. J. ; Fodor , S. P. A. ; Gallop , M. A. Applications of combinatorial technologies to drug discovery, 2: Combinatorial organic synthesis, library screening strategies, and future directions . J. Med. Chem. 1994 , 37 , 1385 – 1401 .
  • Cho , C. Y. ; Youngquist , R. S. ; Paikoff , S. J. ; Beresini , M. H. ; Hebert , A. R. ; Berleau , L. T. ; Liu , C. W. ; Wemmer , D. E. ; Keough , T. ; Schultz , P. G. Synthesis and screening of linear and cyclic oligocarbamate libraries: Discovery of high affinity ligands for GPIIb/IIIa . J. Am. Chem. Soc. 1998 , 120 , 7706 – 7718 .
  • Digenis , G. A. ; Agha , B. J. ; Tsuji , K. ; Kato , M. ; Shinogi , M. Peptidyl carbamates incorporating amino acid isosteres as novel elastase inhibitors. J. Med. Chem. 1986, 29, 1468–1476.
  • Warras , R. ; Walden , P. ; Wiesmuller , K. H. ; Jung , G. Oligocarbamates as MHC class I ligands . Lett. Pept. Sci. 1998 , 5 , 125 – 128 .
  • Cho , C. Y. ; Liu , C. W. ; Wemmer , D. E. ; Schultz , P. G. Cyclic and linear oligocarbamate ligands for human thrombin . Bioorg. Med. Chem. 1999 , 7 , 1171 – 1179 .
  • Owens , R. A. ; Gesellchen , P. D. ; Houchins , B. J. ; Dimarchi , R. D. The rapid identification of HIV protease inhibitors through the synthesis and screening of defined peptide mixtures . Biochem. Biophys. Res. Commun. 1991 , 181 , 402 – 408 .
  • Campbell , D. A. ; Bermak , L. C. ; Burkoth , T. S. ; Patel , D. V. A transition state analog inhibitor combinatorial library . J. Am. Chem. Soc. 1995 , 117 , 5381 – 5382 .
  • Wang , X. ; Huq , I. ; Rana , T. M. HIV-I TAR RNA recognition by an unnatural biopolymer . J. Am. Chem. Soc. 1997 , 119 , 6444 – 6445 .
  • Alsina , J. ; Rabanal , F. ; Chiva , C. ; Giralt , E. ; Albericio , F. Active carbonate resins: Application to the solid phase synthesis of alcohol, carbamate and cyclic peptides . Tetrahedron 1998 , 54 , 10125 – 10152 .
  • Sureshbabu , V. V. ; Sudarshan , N. ; Venkataramanarao , R. Peptidyl carbamates: Efficient synthes using N-Fmoc-β-amino alkoxy carbonyl chlorides/active pentachlorophenyl carbonates as monomeric building blocks . Int. J. Pept. Res. Ther. 2008 , 14 , 149 – 156 .
  • Eckert , H. ; Forster , B. Triphosgene, a crystalline phosgene substitute . Angew. Chem. Int. Ed. Engl. 1987 , 26 , 894 – 895 .
  • Tantry , S. J. ; Sureshbabu , V. V. Synthesis of N α -protected peptide acids by the N-C chain extension employing O, N-bis-trimethylsilyl-amino acids using the mixed anhydride method . Indian J. Chem. 2004 , 43B , 1282 – 1287 .

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.